sc enantioselective allylation and...

18
Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7) Enantioselective Allylation and Crotylation Sc http://dx.doi.org/10.1055/s-0031-1289565 MCCUBBIN, J. A.; MADDESS, M. L.; LAUTENS, M. OS O Sc(OTf) 3 , 10 mol% Et 2 O, 0 °C OH 73% ee 96% N N Si C 6 H 4 Br-4 C 6 H 4 Br-4 Cl + Synlett 2857 2861 2011 19 - , , , Structural Characterisation of Alkoxytitanium Triflate Complexes Ti http://dx.doi.org/10.1002/ejic.201100830 DAVIDSON, M. G.; JOHNSON, A. L. HJ Eur. J. Inorg. Chem. 5151 5159 2010 - , , 33 , Polymerization Catalysts: Zirconium and Hafnium Dithiodiphenolate Zr http://dx.doi.org/10.1002/ejic.201100776 COHEN, A.; GOLDBERG, S.; VENDITTO, S.; KOL, M. HJ Hf Eur. J. Inorg. Chem. 5219 5223 2010 - , , 34 , Enantioselective Synthesis of Heterocyclic β-Amino Alcohols Re http://dx.doi.org/10.1021/jo2019015 MARTIN, M.; EL HELLANI, A.; YANG, J. ; COLLIN, J.; BEZZENINE-LAFOLLEE, S. OS O O + NH 2 OMe O OH N H OMe CH 2 Cl 2, MS 4A 40 °C, 40 h. Cat (7 mol%) ee : 68% Cat : O O O O Y - Li + (THF) 70% Sc Y J. Org. Chem. 9801 9806 2011 76 - , , , 1

Upload: others

Post on 17-Mar-2020

5 views

Category:

Documents


0 download

TRANSCRIPT

Page 1: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Enantioselective Allylation and CrotylationSc

http://dx.doi.org/10.1055/s-0031-1289565

MCCUBBIN, J. A.; MADDESS, M. L.; LAUTENS, M.

OS

O

Sc(OTf)3, 10 mol%

Et2O, 0 °COH

73%ee 96%

N

N

Si

C6H4Br-4

C6H4Br-4

Cl+

Synlett 2857 28612011 19 -, , ,

Structural Characterisation of Alkoxytitanium Trifl ate ComplexesTi

http://dx.doi.org/10.1002/ejic.201100830

DAVIDSON, M. G.; JOHNSON, A. L.

HJEur. J. Inorg. Chem. 5151 51592010 -, , 33 ,

Polymerization Catalysts: Zirconium and Hafnium DithiodiphenolateZr

http://dx.doi.org/10.1002/ejic.201100776

COHEN, A.; GOLDBERG, S.; VENDITTO, S.; KOL, M.

HJ

Hf

Eur. J. Inorg. Chem. 5219 52232010 -, , 34 ,

Enantioselective Synthesis of Heterocyclic ββββ-Amino AlcoholsRe

http://dx.doi.org/10.1021/jo2019015

MARTIN, M.; EL HELLANI, A.; YANG, J. ; COLLIN, J.; BEZZENINE-LAFOLLEE, S.

OS

OO +

NH2

OMe

O

OH

NH

OMeCH2Cl2, MS 4A

40 °C, 40 h.

Cat (7 mol%)

ee : 68%

Cat :O

O O

OY

-

Li+(THF)70%

ScY

J. Org. Chem. 9801 98062011 76 -, , ,

1

Page 2: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Congested Ferrocenyl Polyphosphanes Fe

http://dx.doi.org/10.1021/ic2015379

MOM, S.; BEAUPÉRIN, M.; ROY, D.; ROYER, S.; AMARDEIL, R.; CATTEY, H.; DOUCET, H.; HIERSO, J.-C.

MVI

PR2

PR2R1

R2 PR'2

Fe

Bidendate coordination

Third proximal phosphorus

Cp substituent modulating stericand electronic effects

Ferrocene platform conformation

Inorg. Chem. 11592 116032011 50 -, , 22 ,

Cleavage of Benzyl EtherCo

http://dx.doi.org/10.1021/jo2018284

WANG, B.; YIN, Z.; LI, Y.; YANG,T.-X.; MENG, X.-B.; LI, Z.-J.

OS

OOSi

Co2(CO)8 (0.1 equiv) Me2PhSiH (6 equiv.)

CO (1 atm), benzene, reflux94%6 h.

J. Org. Chem. 9531 95352011 76 -, , ,

Synthesis of IsochromeneRh

http://dx.doi.org/10.1021/jo201923d

MORIMOTO, K.; HIRANO, K.; SATOH,T.; MIURA, M.

OS

+

83%

[Cp*Rh(CH3CN)3][SbF6]2(2 mol%)

Cu(OAc)2 1 equiv

OH

Cl

O

Cl

J. Org. Chem. 9548 95512011 76 -, , ,

Asymmetric Iridium-Catalysed HydrogenationIr

http://dx.doi.org/10.1055/s-0031-1289569CADU, A.; PAPTCHIKHINE, A.; ANDERSSON, P.G.

GJ

CH3O C5H11 CH3O C5H11CH3O C5H11

Na in NH3

S

NPh

PPh2[A-Ir(cod)]BArF (0.5 mol%)

CH2Cl2, H2 (20 bars), 18 h

81% (trans:cis 83:17; ee 98/62%)Practical synthetic procedures; 6 examples, yields: 51-81%(Birch)

BArF = tetrakis(3,5-bis(trifluoromethyl)-phenyl)borate

ANaB

Synthesis 3796 38002011 -, , 23 ,

2

Page 3: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Nickel-Catalyzed Dehydrogenative [4 + 2] Cycloaddition of 1,3-Dienes with NitrilesNi

http://dx.doi.org/10.1021/ja208162w

OHASHI, M.; TAKEDA, I.; IKAWA, M.; OGOSHI, S.

MVI

N N

Ph

Ph N NPh

Ph Ph

Ph8 eq.

10 mol% Ni(COD)240 mol% PCy3

Toluene, 130°C 60h, 80%

J. Am. Chem. Soc. 18018 180212011 133 -, , 45 ,

Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple OlefinsNi

http://dx.doi.org/10.1021/ja209235d

MATSUBARA, R.; GUTIERREZ, A. C.; JAMISON, T. F.

MVI

Cl

OPh

BrBr

OPh

10 mol% Ni(COD)220 mol% PCy2Ph

6 eq. Et3N, RT1.75 eq. Et3SiOTf

97%

J. Am. Chem. Soc. 19020 190232011 133 -, , 47 ,

Palladium-Catalyzed Regioselective g-Mono- and Diarylation of Acrylamide DerivativesPd

http://dx.doi.org/10.1002/adsc.201100373

YU, M.; XIE, Y.; LI, J.; ZHANG, Y.

HD

ArHN

OAr'X

Pd(OAc)2 10 %, PPh3 20 %

t-BuONa, toluene, 110°C, 1 h

Ar'

Ar'ArHN

O ArHN

OAr'

or+

Ar = C6F5

Adv. Synth. Catal. 2933 29382011 353 -, , 16 ,

Highly Stereo- and Regioselective Trisubstituted Alkene Synthesis of Wide ApplicabilityPd

http://dx.doi.org/10.1002/adsc.201100420

XU, S.; LEE, C.-T.; RAO, H.; NEGISHI, E.

HD

R1 X1) HBY2

2) pinacol BpinR1

X

H

1) R2ZnBr

2) R3X R3R1R2

HPd cross-coupling≥98 % Z ≥98 % isomerically pur

X = Br,I Y = Br, Ipc

Zn

Adv. Synth. Catal. 29816 29872011 353 -, , 16 ,

3

Page 4: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Palladium(II)-Catalyzed Direct ortho-C-H Acylation of AnilidesPd

http://dx.doi.org/10.1002/adsc.201100472

CHAN, C.-W.; ZHOU, Z.; YU, W.-Y.;

HD

N

R2

O

R1

GF

N

R2

O

R1

GFR3

O

H

Pd(OAc)2 5 %

TBHP, TFAtoluene, 40°C, 3 h

OR3

+

21 examples

45-87 %

Adv. Synth. Catal. 2999 30062011 353 -, , 16 ,

Palladium-Catalyzed Carbonylation of Diols to Cyclic CarbonatesPd

http://dx.doi.org/10.1002/adsc.201100240

PEARSON, D. M.; CONLEY, N. R.; WAYMOUTH, R. M.

HD

R4R1

R2 R3

HO OH

R4R1

R2 R3

O O

O

(neocuproine)Pd(OAc)2 3 %

NCS, NaOAcCO (1 atm), CH3CN, 55°C

Adv. Synth. Catal. 3007 30132011 353 -, , 16 ,

Sonogashira Coupling Reaction of Unreactive Aryl ChloridesPd

http://dx.doi.org/10.1002/adsc.201100747

LEE, D.-H.; KWON, Y.-J.;JIN, M.-J.

HD

RCl

RR'+ R'

Catalyst 0.5 %

piperidine, TBABDMF-H2O, 50°C

PdNN

Ar ArEt3P CH3

Catalyst :

Ar = 2,6-(CH3)2C6H3

Adv. Synth. Catal. 3090 30942011 353 -, , 17 ,

New Palladium-Catalyzed Cascades: 4-exo-dig Cyclocarbopalladation ReactionPd

http://dx.doi.org/10.1002/adsc.201100465

CHARPENAY, M.; BOUDHAR, A.; SIBY, A.; SCHIGAND, S.; BLOND, G.; SUFFERT, J.

HD

Br

XO

O

O

O

X

R

H RPd(OAc)2 5 %, PPh3 10 %

CuI 10 %, i-Pr2NH100°C, microwave

X = OH, NR1R2

+

Adv. Synth. Catal. 3151 31562011 353 -, , 17 ,

4

Page 5: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Palladium-Catalyzed Direct Synthesis of Organoboronic AcidsPd

http://dx.doi.org/10.1002/anie.201102384

PILARSKI, L. T.; SZABÓ, K. J.

GJPAngew. Chem. Int. Ed. 8230 82322011 50 -, , ,

Powerful Insight into Catalytic Mechanisms through Simultaneous Monitoring of Reactants,Products, and Intermediates

Pd

http://dx.doi.org/10.1002/anie.201102630

VIKSE, K. L.; AHMADI, Z.; MANNING, C. C.; HARRINGTON, D. A.; MCINDOE, J. D.

GJPAngew. Chem. Int. Ed. 8304 83062011 50 -, , ,

Palladium-Catalyzed Borylation of Sterically Demanding Aryl Halides with a Silica-SupportedCompact Phosphane Ligand

Pd

http://dx.doi.org/10.1002/anie.201103224

KAWAMORITA, S.; OHMIYA, H.; IWAI, T.; SAWAMURA, M.

GJPAngew. Chem. Int. Ed. 8363 83662011 50 -, , ,

Stereospecific Palladium-Catalyzed Decarboxylative C(sp3)-C(sp2) Coupling of2,5-Cyclohexadiene-1-carboxylic Acid Derivatives with Aryl Iodides

Pd

http://dx.doi.org/10.1002/anie.201103450

CHOU, C.-M.; CHATTERJEE, I.; STUDER, A.

GJPAngew. Chem. Int. Ed. 8614 86172011 50 -, , ,

5

Page 6: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Palladium(0)-Catalyzed Intermolecular Amination of Unactivated C-H BondsPd

http://dx.doi.org/10.1002/anie.201102880

PAN, J.; SU, M.; BUCHWALD, S. L.

GJPAngew. Chem. Int. Ed. 8647 86512011 50 -, , ,

Palladium(II)-Catalyzed Selective Monofluorination of Benzoic Acids Using a PracticalAuxiliary: A Weak-Coordination Approach

Pd

http://dx.doi.org/10.1002/anie.201102985

CHAN, K. S. L.; WASA, K.; WANG, X.; YU, J.-Q.

GJPAngew. Chem. Int. Ed. 9081 90842011 50 -, , ,

Domino Rhodium-Catalyzed Alkyne Arylation/Palladium-Catalyzed N Arylation: AMechanistic Investigation

Pd

http://dx.doi.org/10.1002/anie.201103692

PANTELEEV, J.; ZHANG, L.; LAUTENS, M.

GJP

Rh

Angew. Chem. Int. Ed. 9089 90922011 50 -, , ,

Cathechols from PhenolsPd

http://dx.doi.org/10.1021/ja2089102

HUANG, C.; GHAVTADZE, N.; CHATTOPADHYAY, B.; GEVORGYAN, V.

CJM

RO

Si

OH

tButBu

1) Pd(OPiv)2 5 mol%PhI(OAc)2 2 equiv

PhMe, 100 °C

2) TBAF / THFR

OH

OH

Si

J. Am. Chem. Soc. 17630 176332011 133 -, , 44 ,

6

Page 7: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Hydrogenolysis of Alcoxides and PhenoxidesPd

http://dx.doi.org/10.1021/ja205824q

FULMER, G. R.; HERNDON, A. N.; KAMINSKY, W.; KEMP, R. A.; GOLDBERG, K. I.

CJM

PtBu2

PtBu2

Pd OR+ H2

- H2

PtBu2

PtBu2

Pd H

J. Am. Chem. Soc. 17713 177262011 133 -, , 44 ,

Ligand Modification in Aryl Fluoride SynthesisPd

http://dx.doi.org/10.1021/ja208461k

MAIMONE, T. J.; MILNER, P. J.; KINZEL, T.; ZHANG, Y.; TAKASE, M. K.; BUCHWALD, S. L.

CJM

MeO

OMe

P(t-Bu)2i-Pr i-Pr

i-Pr

Pd(0), AgF

n-Bu Br MeO

OMe

P(t-Bu)2i-Pr i-Pr

i-Prn-Bu

Ligand invovedin the C-F reductive

elimination

Ar-Br

Ar-F

J. Am. Chem. Soc. 18106 181092011 133 -, , 45 ,

Carbonylations with Silacarboxyic AcidsPd

http://dx.doi.org/10.1021/ja208652n

FRIIS, S. D.; TAANING, R. H.; LINDHART, A. T.; SKRYDSTRUP, T.

CJM

Si OHMe

O

Ph Ph

KF

Dioxane, 40 °C

bench-stable, solid CO-releasing molecule

Applications in Pd-catCarbonylative X-coupling

reactions (amino and alkoxy carbonylationscarbonylative Heck and Sonogashira couplings...)

CO

J. Am. Chem. Soc. 18114 181172011 133 -, , 45 ,

Amino-Acid Ligand in C(sp2)-H Bond Activations with Aryl Boron ReagentsPd

http://dx.doi.org/10.1021/ja203978r

ENGLE, K. M.; THUY-BOUN, P. S.; DANG, M.; YU, J. Q.

CJM

CO2H

H

Ar-BF3KPd(OAc)2 5 mol%

Ac-Ile-OH 10 mol%

BQ 5 mol%, Ag2CO3 1 equiv.KHCO3 2 equiv., t-AmylOH 110 °C

R CO2H

ArR

B

J. Am. Chem. Soc. 18183 181932011 133 -, , 45 ,

7

Page 8: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Allylic Oxidation of cis-Vinylsilanes: Influence of the Oxidant on the StereoselectivityPd

http://dx.doi.org/10.1021/ja2089102

CHECK, C. T.; HENDERSON, W. H.; WRAY, B. C.; VANDEN EYNDEN, M. J.; STAMBULI, J. P.

CJM

RSiEt3

n

Pd(OAc)2 2 mol%AcOH 90 °C

BQ

RSiEt3n

OAcPd(OAc)2 2 mol%AcOH 90 °C

PhI(OAc)2

RSiEt3

n

OAc

Z/E 5:1 E/Z > 19:1

J. Am. Chem. Soc. 18503 185062011 133 -, , 46 ,

C-H ArylationPd

http://dx.doi.org/10.1021/ja208068w

KALYANI, D.; MCMURTREY, K. B.; NEUFELDT, S. R.; SANFORD, M. S.

CJM

NR1

R2+

[Ar-N2]BF4

Ru(bpy)3Cl2·6H2O2.5 mol%

26 W lightbulb

MeOH, rtR3

Pd(OAc)2

10 mol%

NR2

Ar

R1Ru

J. Am. Chem. Soc. 18566 185692011 133 -, , 46 ,

C3-Selective Direct Arylation of Pyridines Pd

http://dx.doi.org/10.1021/ja209510q

YE, M.; GAO, G.; EDMUNDS, A. J. F.; WORTHINGTON, P. A.; MORRIS, J. A.; YU, J. Q.

CJM

NR1

H+ R2

XPd(OAc)2 5 mol%

Phen 15 mol%

Cs2CO3 3 equiv140 °CXs.

NR1

R2

J. Am. Chem. Soc. 19090 190932011 133 -, , 47 ,

Pd-Josiphos-catalyzed Enantioselective a-Arylation of Silyl Ketene AcetalsPd

http://dx.doi.org/10.1021/om200945q

KOBAYASHI, K.; YAMAMOTO, Y.; MIYAURA, N.

PB

OTMS

R1 OR2

Ar-X

Pd(OAc)2 / ligand

TlOAcAr

R1

CO2R2

up to 91% ee

ligand = Fe

PR2R'2P

*

Organometallics, 6323 6272011 30 -, , 22 ,

8

Page 9: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Synthesis of Arylhydrazines.Pd

http://dx.doi.org/10.1055/s-0030-1260337.

MA, F.-F.; PENG, Z.-Y.; LI, W-F.; XIE, X.-M.; ZHANG, Z.

MJSynlett 2555 25582011 -, , 17 ,

Synthesis of Carbazolo[1,2-b]carbazoles.Pd

http://dx.doi.org/10.1055/s-0030-1289514.

CHAITANYA, T. K.; NAGARAJAN, R.

MJSynlett 2559 25612011 -, , 17 ,

Synthesis of 2-Substituted 3-Hydroxymethylbenzo[b]furans.Pd

http://dx.doi.org/10.1055/s-0030-1289519.

WANG, H.; HAN, X.; LU, X.

MJSynlett 2590 25942011 -, , 17 ,

Allylic oxidation. Synthesis of Vinyllactones. Pd

http://dx.doi.org/10.1055/s-0031-1289549.

BISCHOP, M.; PIETRUSZKA, J.

MJSynlett 2689 26922011 -, , 18 ,

9

Page 10: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Asymmetric Oxetane Synthesis.Pd

http://dx.doi.org/10.1055/s-0031-1289540.

MIKAMI, K.; AIKAWA, K.; AIDA, J.

MJSynlett 2719 27242011 -, , 18 ,

Asymmetric Domino Allylstannylation-Heck Reaction.Pd

http://dx.doi.org/10.1055/s-0031-1289539.

SCHÜTTE, J.; YE, S.; SCHMALZ, H.-G.

MJ

Sn

Synlett 2725 27292011 -, , 18 ,

Intramolecular Hydroarylation.Pd

http://dx.doi.org/10.1055/s-0031-1289545.

NANDAKUMAR, A.; BALAKRISHNAN, K.; PERUMAL, P. T.

MJSynlett 2733 27392011 -, , 18 ,

Enantioenriched Stereogenic Centers via Ni- and Pd-Catalyzed Reactions.Pd

http://dx.doi.org/10.1055/s-0031-1289871.

TAYLOR, B. L. H.; JARVO, E. R.

MJ

Ni

Synlett 2761 27652011 -, , 19 ,

10

Page 11: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Review: From Vinyl Chloride Derivatives.Pd

http://dx.doi.org/10.1055/s-0031-1289862

GUINCHARD, X.; ROULLAND, E.

MJ

B

Synlett 2779 27882011 -, , 19 ,

Alkynylations of Heteroarenes and Double Arylations of Diynes.Pd

http://dx.doi.org/10.1055/s-0031-1289861.

SALEH, S.; PICQUET, M.; MEUNIER, P.; HIERSO, J.-C.:

MJSynlett 2844 28482011 -, , 19 ,

Copper(I)-Catalyzed Deacetylenative CouplingCu

http://dx.doi.org/10.1002/chem.201102710

KIM, Y.; NAKAMURA, H.

HD

R1

NR3R2

CuCl 20 %

THF, 130°CSealed vial tube

R1

N R1

N

R3R2

R3R2

13 examples37-90 %

Chem. Eur. J. 12561 125632011 17 -, , 45 ,

Enantioselective Henry ReactionCu

http://dx.doi.org/10.1002/chem.201102136

KODAMA, K.; SUGAWARA, K.; IROSE, T.

HD

R H

O

CH3NO2

Cu(OAc)2. H2O 10 %, L 10 %

DABCO 2 %, EtOH, 0°C, 24hNH

NMe2

Ar

RNO2

OH

+ L :

Ar = 1-Naphtylee up to 91 %

Chem. Eur. J. 13584 135922011 17 -, , 48 ,

11

Page 12: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Enantioselective Alkynylation of Isochroman AcetalsCu

http://dx.doi.org/10.1021/ja207585p

MAITY, P.; SRINIVAS, H. D.; WATSON, M. P.

HD

O

OMe R2

O

R2

Cu(MeCN)4PF6 10%L 12 %, TMSOTf

i-Pr2NEt, Et2O-22°C, 12 h

O

N N

O

Bn Bn

Me Me

+ L :

R1 R1

ee up to 94 %

J. Am. Chem. Soc. 17142 171452011 133 -, , 43 ,

Direct Access to ß-Oxodiazo Compounds Cu

http://dx.doi.org/10.1021/ja208965b

BARLUENGA, J.; LONZI, G.; RIESGO, L.; TOMAS, M.; LOPEZ, L. A.

HD

EWG R2

R1

N2

Ph-I=OCu(OTf)2 5 %

CH3CN, RT+ R1 EWG

R2

O N2

J. Am. Chem. Soc. 18138 181412011 133 -, , 45 ,

Stereoselective Synthesis of Polyfunctional Tetrasubstituted Alkenyl SulfidesCu

http://dx.doi.org/10.1055/s-0030-1260210DUNST, C.; METZGER, A.; ZABURDAEVA, E.A.; KNOCHEL, P.

GJ

SCH3

NC

Cl

Zn

SCH3

I

Cl

NC

22 examples; carbocupration ofalkynyl sulfides with aryl and

benzylic diorganozincs+

2

.2MgX2.LiCl

2 CuCN.2 LiCl

THF, -20°C, 16 h

70% (E/Z 99:1)

(1.5 equiv)

ZnLi

Synthesis 3453 34622011 -, , 21 ,

One-Pot Synthesis of Imidazo[1,2-a]pyridinesCu

http://dx.doi.org/10.1055/s-0030-1260255MISHRA, S.; GHOSH, R.

GJ

H

O

N NH2

N

NPh

Ph28 examples, yields: 60-91%

+ +NaHSO4.SiO2

toluene, reflux, 12 h

CuI (5 mol%)

91%

Synthesis 3463 34702011 -, , 21 ,

12

Page 13: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Synthesis of 1N-Alkyl-4-aryl-1,2,3-triazolesCu

http://dx.doi.org/10.1055/s-0030-1260256LADOUCEUR, S.; SOLIMAN, A.M.; ZYSMAN-COLMAN, E.

GJ

CH3OBr

N

N

NCH3O

Practical synthetic procedures; multicomponent one-pot click protocol; 25 examples, yields:38-96%

+TMS

NaN3, CuSO4 (20 mol%)

1:1 MeOH, Et2O, rt, 18 h

K2CO3 (1.8 equiv)

61%pyridine, ascorbic acid

Synthesis 3604 36112011 -, , 22 ,

Synthesis of Mono- and Bis-N-Heterocyclic Carbene Copper(I) ComplexesCu

http://dx.doi.org/10.1055/s-0030-1260250LE GALL, T.; BALTATU, S.; COLLINS, S.K.

GJ

N N

CO2

MesMes

N N

Cu

MesMes

N N MesMes

I

13 examples, yields: 41-91%;decarboxylative generation

of carbenes

+

_

+ _THF, 60°C, 24 h

CuI (0.5 equiv)

77%

Synthesis 3687 36912011 -, , 22 ,

One-Pot Synthesis of Pyrazolo[3,4-b]indoles and New Isoxazolo[5,4-b]indolesCu

http://dx.doi.org/10.1055/S-0031-1289572KUMAR, A.S.; RAO, P.V.A.; NAGARAJAN, R.

GJ

NCl

CH3

O

Et

N

CH3

Ph

Et

a) PhNHNH2, NMP

MW, 120°C, 10 min

b) CuI (0.05 mol%), K2CO3

MW, 120°C, 10 min

Optimized conditions26 examples, yields: 82-96%

Intramolecular C–N/C–Obond formation92%

Synthesis 3878 38862011 -, , 23 ,

N-Arylation of Nucleobases and N-Heterocyclic CompoundsCu

http://dx.doi.org/10.1055/s-0030-1260236RAD, M.N.S.; BEHROUZ, S.; DOROODMAND, M.M.; MOGHTADERIA, N.

GJ

NH

NH

O

O

I

SiO2-OSO

3Cu N

H

N O

O

+(0.05 mol%)

DBU, DMF, reflux, 8 h60%

Ullmann-type N-arylation catalysis by Cu nanoparticle-doped silica cuprous sulfate (preparation given); 22 examples, yields: 35-77%

Synthesis 3915 39242011 -, , 23 ,

13

Page 14: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Allylation of Arenes with Allylic Alcohols.Ag

http://dx.doi.org/10.1055/s-0031-1289548.

CHEN, G.-Q.; XU, Z.-J.; CHAN, S. L.-F.; ZHOU, C.-Y.; CHE, C.-M.

MJSynlett 2713 27182011 -, , 18 ,

Nanoparticles in Amide SynthesisAu

http://dx.doi.org/10.1021/ja2080086

SOULÉ, J.-F.; MIYAMURA, H.; KOBAYASHI, S.

CJM

R OH + HNR1R2

PICB-Au nanoparticlesNaOH 1 equiv

O2 BalloonTHF / water 40 °C

R NR1R2

O

J. Am. Chem. Soc. 18550 185532011 133 -, , 46 ,

Hydroamination with New Acyclic Aminoxycarbene-Gold ComplexesAu

http://dx.doi.org/10.1021/om200602k

SEO, H.; SNEAD, D.R.; ABBOUD, K.A.; HONG, S.

PB

NH

RR'

R''

R'''

O

NHR''''

LAuCl (5-10 mol%)

AgOTf (5-10 mol%)

dioxane or MeOH

N OR3

Au

Cl

R1

R2N

RR'

R''

R'''

O

NHR''''

R1 = iPr, adamentyl, 2,6-di-iPr-phenyl, 2,6-di-Me-phenyl

R2 = iPr, Ph, Cy, adamentyl

R3 = adamentyl,2,6-di-iPr-phenyl

LAuCl =

Organometallics, 5725 57302011 30 -, , 21 ,

A Zinc(II) Catalyst System for the Conia-Ene Reaction of Alkynyl-AminomalonatesZn

http://dx.doi.org/10.1002/adsc.201100401

HESS, W.; BURTON, J. W.

HD

N

X

R1CO2Et

CO2Et

( )n

R2

NR1

X R2

EtO2C CO2Et

NR1

X

EtO2C CO2Et

R2

n = 1, 2, 3 n = 0

( )n

orZnCl2 10 %

ClCH2CH2Cl100°C, 15 h

X = O, H2

Adv. Synth. Catal. 2966 29702011 353 -, , 16 ,

14

Page 15: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Synthesis of Diaryl Ketones via a Phosphine-Free Fukuyama ReactionZn

http://dx.doi.org/10.1039/C1CC16114H

KUNCHITHAPATHAM, K.; EICHMAN, C. C.; STAMBULI, J. P.

MVI

F F

SEt

O

MeO ZnCl

F F

O

OMe1.2 eq.

1 mol% Pd(dba)2

Toluene, 23°C

82%

Chem. Commun. 12679 126812011 47 -, , 47 ,

Reactions of ZnR2 CompoundsZn

http://dx.doi.org/10.1002/chem.201101997

DRANKA, I.; KUBISIAK, M.; JUSTYNIAK, I.; LESIUK, M.; KUBICKI, M.; LEWIN´ SKI, J.

HJChem. Eur. J. 12713 127212010 17 -, , ,

Cationic Cyclopentadienyl Zinc ComplexesZn

http://dx.doi.org/10.1002/chem.201102699

CHILLECK, M. A.; BRAUN, T.; BRAUN, B.

HJChem. Eur. J. 12902 129052010 46 -, , ,

Micellar Catalysis : Negishi-like Cross-couplings in Water at Room TemperatureZn

http://dx.doi.org/10.1021/om200846h

DUPLAIS, C.; KRASOVSKIY, A.; LIPSHUTZ, B.H.

PB

R Br BrR'

Zn / TMEDA

PdCl2(Amphos)2 (0.5 mol%)

4% surfactant-H2O, rt

(surfactant = Brij30)

RR'

+

Organometallics, 6090 60972011 30 -, , 22 ,

15

Page 16: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Preparation of Pyrone DerivativesZn

http://dx.doi.org/10.1055/s-0031-1289855

RIEKE, R. D.; KIM, S.-H.

OS

THF, rt, 30 min

Pd(PPh3)4 (1mol%)Cl

O

O

O

BrZn +

O O

COAr

94%

Synlett 2867 28712011 19 -, , ,

Addition of Diethylzinc to AldehydesZn

http://dx.doi.org/10.1055/s-0030-1260230WERNER, T.; RIAHI, A.M.; SCHRAMM, H.

GJ

H

O

F Et2Zn

OHF

Et

27 examples, yields: 26-99%; phosphonium salt catalysis

+

92%

Bu4PCl (7 mol%)

toluene, 23°C, 24 h

Synthesis 3482 34902011 -, , 21 ,

Synthesis of Coumarins and NeoflavonesZn

http://dx.doi.org/10.1055/s-0031-1289576LEAO, R.A.C.; DE MORAES, P.DE F.; PEDRO, M.C.B.C.; COSTA, P.R.R.

GJ

OH OH

OH

OOH

OH CH3

O

CH3

O

OEt

37 examples; hydroarylation of acetylenic esters with phenols; solvent-free conditions

+ZnCl2 (5 mol%)

100°C

84%

Synthesis 3692 36962011 -, , 22 ,

Cyclization of Homopropargyl AzidesHg

http://dx.doi.org/10.1055/s-0031-1289566

YAMAMOTO,H.; SASAKI, I.; MIZUHO, M.; KARASUDANI, A. ; IMAGAWA, H.; NISHIZAWA, M.

OS

C5H11

N3 HNC5H11

CH3NO2, rt, 10 min

(20mol%)

99%

Si

HgOTf

Synlett 2815 28182011 19 -, , ,

16

Page 17: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

One-Pot Epoxide RearrangementBi

http://dx.doi.org/10.1021/jo201478d

LAMBERT, R. F.; HINKLE, R. J.; AMMANN, S. E.; LIAN, Y.; LIU, J.; LEWIS, S. E.; PIKE, R. D.

OS

SiMe3

OH

+ O

66%

Bi(OTf)3.nH2O (5 mol%)O

CH2Cl2, 0 °C to rt

J. Org. Chem. 9269 92772011 76 -, , ,

Aryl Diazonium versus Iodonium Salts: Preparation, Applications and Mechanisms Rv

http://dx.doi.org/10.1002/adsc.201100531

BONIN, H.; FOUQUET, E.; FELPIN, F.-X

HD

ArN2X versus Ar2IXSuzuki-Miyauracross coupling Ar-Ar'Ar'B(OR)2+ 77 references

Pd

Adv. Synth. Catal. 3063 30842011 353 -, , 17 ,

Transition-Metal-Catalyzed Rearrangements of Small CycloalkanesRv

http://dx.doi.org/10.1055/s-0030-1260233AÏSSA, C.

GJ

X

R

MX

M

R

XM R

Regioselectivity trends inβ-carbon elimination

Review with ~ 140 references

( )n ( )n ( )nand/or

R � H

X = C, N, O

n = 0, 1

Synthesis 3389 34072011 -, , 21 ,

Direct Amination of Azole C–H BondsRv

http://dx.doi.org/10.1055/s-0030-1260231ZHANG, M.

GJ

Short review with 75 references

Copper catalysis

Cu

Synthesis 3408 34172011 -, , 21 ,

17

Page 18: Sc Enantioselective Allylation and Crotylationddata.over-blog.com/xxxyyy/3/59/81/73/Annee-2011/Cahier2011-7-.pdfBibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

Bibliographic Notebooks For Organometallic Chemistry 2011, 29, ( 7)

The Oxidation of Amides to ImidesRv

http://dx.doi.org/10.1055/s-0030-1260237SPERRY, J.

GJ

N

O H H

R

N

O O

RReview (in part)

RuCrCu

Synthesis 3569 35802011 -, , 22 ,

Synthesis and Application of [2.2]Paracyclophane Derivatives in CatalysisRv

http://dx.doi.org/10.1055/s-0031-1289296PARADIES, J.

GJ

Review (in part)Xn Yn

ZnPdRh

Synthesis 3749 37662011 -, , 23 ,

Intramolecular Azide–Alkyne Cycloaddition ReactionsRv

http://dx.doi.org/10.1055/s-0031-1289295MAJUMDAR, K.C.; RAY, K.

GJ

Short review (in part)Synthesis of 1,2,3-triazole-fused heterocycles

Synthesis 3767 37832011 -, , 23 ,

18