Imprimatur:
Date, Signaturetc1818st.fm 10/29/18
Accounts andRapid Communications in Chemical Synthesis
2018Vol. 29, No. 18
NovemberSyn lett
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Synlett 2018, 29, 2331–2336DOI: 10.1055/s-0037-1610432
S. L. JohnsonL. A. CombeeM. K. Hilinski*University of Virginia, USA
Syn lett
as
Organocatalytic Atom-Transfer C(sp3)–H Oxidation
R1
R2R3
HO N
N
O N
N N
O O
O NR
catalytic
[O] or [N]
site-selectiveoxidation
i-Pr
Me H
Me
NHTs
NPhth
AcO
RMe
Me
H
H
H
OH
C–H hydroxylation
C–H amination
Synpacts
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Synlett 2018, 29, 2337–2341DOI: 10.1055/s-0037-1610550
L. ZhangY. Wang*Shandong University, P. R. of China
Uncovering Multifaceted Iodonium Ylides: Versatile Reactivity Enables Cyclization of Simple Arylamines
+
NR1OC CO2R2
IPh R
N
R1OC CO2R2
R
without modification of amineswithout a transition metalwithout additional hydrogen acceptorwithout additional initiator/oxidant
Exceptional Iodonium Ylide = Electron Transfer + Hydrogen Abstraction + Nucleophilic Addition
Synpacts
2337
VI
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Synlett 2018, 29, 2342–2361DOI: 10.1055/s-0037-1609584
S. Kotha*K. Lahiri*G. SreevaniIndian Institute of Technology-Bombay, IndiaV. K. Krishna Menon College of Commerce & Economics, India
Syn lett
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s st
Design and Synthesis of Aromatics through [2+2+2] Cyclotrimerization
Rh(
PP
h 3) 3
Cl
CpCo(
CO) 2
Mo(CO)6
OH
OHCO2Et
TsN
TMS
TMS
R
R
RO
O
O
Br
Rh(PPh3 )3 Cl
Cp*RuCl(cod) CO2Me
MeO2C
MeO2C
CO2Me
O
O
O
O
N
N
O
O
O
BocNsteps
O
O
O
O
OH
PBr3
[CpRu(C10H
8)] +Cl –
Mo(
CO
) 6
HO
OH
O
MeN
NN
Hsp90 InhibitorAT13387
Br
[2+2+2]Cycloaddition
Cl2(PPh3)2Ru=CHPh
Account
2342
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Synlett 2018, 29, 2362–2371DOI: 10.1055/s-0037-1609907
S. P. PanchalB. K. ReddyV. G. Anand*Indian Institute of Science Edu-cation and Research, India
as
Syntheses and Redox Chemistry of Antiaromatic Core-Modified Isophlorinoids
HN
NNH
NHN
N
NH
N
OO
OO
SS
S
SO
SO
SO
HNO
O
Porphyrin N-Confused Porphyrin
Isophlorins and Confused Isophlorins
Account
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Synlett 2018, 29, 2372–2376DOI: 10.1055/s-0037-1611000
Y. FujiwaraR. MutaK. SatoH. HaramuraY. YamadaT. Hanamoto*Saga University, Japan
A γ-Fluoro β-Acetoxypropyl Sulfonium Salt as an Equivalent of a (Fluoromethyl)vinyl Sulfonium Salt: Reagent for the Facile Synthesis of Monofluoromethylated Cyclopropanes or Aziridines
H2FCSPh2•OTf
OAc+ –
H2FC
SPh2•OTf+ –
N
Ts
H2FC
H2FC
EWG2
EWG1
EWG2
EWG1
TsNH2
transient
baseup 98% yield 9 examples
96% yield
free-flowing solid
Letter
2372
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Synlett 2018, 29, 2377–2380DOI: 10.1055/s-0037-1611024
S. WatanabeM. IshikawaT. NomuraT. FukuyamaS. Yokoshima*Nagoya University, Japan
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Total Synthesis of Lycoposerramine-R
O
Me
OH
O
MgBr
HH
O
On-Bu
Ph
S
H2N
O
OMe
HN
H
HN
H
O
lycoposerramine-R
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Synlett 2018, 29, 2381–2384DOI: 10.1055/s-0037-1610632
C. DaiY. ShenQ. Wang*East China University of Science and Technology, P. R. of China
as
Two Propanediurea-based Cucurbituril Analogues: Bis-ns-TD[8] and NH-ns-TD[4]
Letter
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Synlett 2018, 29, 2385–2389DOI: 10.1055/s-0037-1610995
M. Minakawa*K. WatanabeS. ToyodaY. UozumiYamagata University, Japan
Iridium-Catalyzed Direct Cyclization of Aromatic Amines with Diols
HN
NH2
R2
R1
+ HO OH
N
N
R2
R1
5 examples
7 examples
73–83% yield
26–76% yield
+ 2 H2O
R1 = H, OMe, Me, F, Cl
R2 = H, 4-OMe, 4-Me, 4-F, 3-F, 4-Cl, 4-CF3
+ 4 H2O
catalyst: IrCl3ligand: BINAP
mesitylene 165 °C
18 h
Letter
2385
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Synlett 2018, 29, 2390–2395DOI: 10.1055/s-0037-1611061
L.-M. Chen*Z.-H. LiuX.-F. NieX.-Q. GuoT.-R. Kang*Chengdu University, P. R. of ChinaChina West Normal University, P. R. of China
Syn lett
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Straightforward Synthesis of Triester-Substituted Pyrrolizidines by a Three-Component Reaction of β,γ-Unsaturated α-Keto Esters, Proline, and Maleates
Ar
N CO2R3
CO2R3MeO2C
Ar
O
O
OR2
NH
CO2H
+
CO2R3
CO2R3DMF
80 °C14 examplesup to 86% yield and 93:7 drester groups in trans-orientationone quaternary center
Letter
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Synlett 2018, 29, 2396–2403DOI: 10.1055/s-0037-1609948
Y. Liu*Q.-L. WangB.-Q. XiongP.-L. ZhangC.-A. YangY.-X. GongJ. LiaoQ. Zhou*Hunan Institute of Science and Technology, P. R. of China
as
Visible-Light-Mediated ipso-Carbosulfonylation of Alkynes: Synthesis of 3-Sulfonylspiro[4,5]trienones from Propiolamides and Sulfonyl Chlorides under Transition-Metal-Free Conditions
+Z
N
R2
R3
O
ON
R2
R3
O
R4 S Cl
O
O
SR4
O
O
R1 R1
Z = OR, SMe, F, Cl, Br, I
Transition-metal-free
visible light
R4 = Ar, heterocyclic, aliphaticH2O
44 examples, up to 95%yield
Transition-metal-free Broad substrates scope
High yields Easily handled conditions
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Synlett 2018, 29, 2404–2407DOI: 10.1055/s-0037-1609629
T. Hirashita*Y. SugiharaS. IshikawaY. NaitoY. MatsukawaS. ArakiNagoya Institute of Technology, Japan
Revisiting Sodium Hypochlorite Pentahydrate (NaOCl·5H2O) for the Oxidation of Alcohols in Acetonitrile without Nitroxyl Radicals
OH
R2R1
O
R2R1
NaOCl (Bleach)TEMPO, KBrCH2Cl2
NaOCl·5H2OTEMPO, Bu4NHSO4CH2Cl2
NaOCl·5H2ONo CatalystCH3CN
1° > 2° 1° < 2°1° = 2°
benzylic and aliphatic secondary alcohols
NaOCl·5H2O
CH3CN up to 97% yield
10 examples
Letter
2404
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Synlett 2018, 29, 2408–2411DOI: 10.1055/s-0037-1611019
M. KatadaK. KitaharaS. IwasaK. Shibatomi*Toyohashi University of Technology, Japan
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Catalyst-Free Decarboxylative Fluorination of Tertiary β-Keto Carboxylic Acids
easily accessible to various tertiary fluoridescatalyst-free reaction
O
R1CO2H
R2 R3 – CO2
O
R1F
R2 R3N
N
F
Cl
2BF4
+–
++
14 examples56–93% yield
R1 = alkyl, arylR2, R3 = alkyl, allyl, benzyl
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Synlett 2018, 29, 2412–2416DOI: 10.1055/s-0037-1611012
Z. SiposK. Kónya*University of Debrecen, Hungary
as
Synthesis of 1,3-Azol-2-yl O-Heterocycles by Microwave-Irradiation-Assisted Direct C–H Functionalization
O
Br
ON
Y
Y = NMe, O, S MW-assisted conditions
+N
Y
25 examplesup to 88% yield
O-heterocycles:flavones,
chromone, coumarin,
chromanones
C-2 selective coupling of 1,3-azoleswith O-heterocycles
Pd catalyst
CuIDMF
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Synlett 2018, 29, 2417–2421DOI: 10.1055/s-0037-1610298
M. S. AziziJ. Cossy*PSL Research University, CNRS, France
Selective Deprotection of N-Tosyl Alkoxyamines Using Bistrifluoromethane Sulfonimide: Formation of Oxime Ethers
ONH
SO O HNTf2 (10 mol%)
CH2Cl2, 40 °C, 18 h ONR R+ H
O
R'R'
metal-free
R' = H, OMe
+ TsOH
40–73%
10 examples
R =
Ph
Letter
2417
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Synlett 2018, 29, 2422–2426DOI: 10.1055/s-0037-1611227
N. YiY. XiongQ. HuangN. YanY. XieD. LanZ. YiC.-T. AuB. Yi*J. Xiang*Hunan Institute of Engineering, P. R. of ChinaHunan University, P. R. of China
Syn lett
Syn lett
Copper-Catalyzed Oxidative Self-Coupling of α-Amino Carbonyl Compounds for the Synthesis of Tetrasubstituted 1,4-Enediones
20 examplesup to 84% yield
high stereoselectivity
Cu(acac)2, DTBP
DBU, CH3CN, 100 °CPh
O
NR2
R1
N N
Ph
O
Ph
O
R1 R1
R2 R21
2, Z-isomerR1, R2 = alkyl, aryl
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Synlett 2018, 29, 2427–2431DOI: 10.1055/s-0037-1611001
N. RiemerC. CoswigM. ShipmanB. Schmidt*Universität Potsdam, Germany
as
Palladium-Catalyzed Cross-Coupling of Arenediazonium Salts with Organoindium or Organobismuth Reagents
N2 BF4 Pd-catalyzed
Organo-In reagents
Organo-Bi reagents• 22 examples• 35–92% yield• R1 = Ac, NO2, NHAc, F, OH, OCH3, Br, CN, CO2CH3
• R2 = OCH3, F
R1
R2
R1cross-coupling
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Synlett 2018, 29, 2432–2436DOI: 10.1055/s-0037-1610293
B. SunZ. YanC. Jin*W. Su*Zhejiang University of Technology, P. R. of China
(Diacetoxyiodo)benzene-Mediated Transition-Metal-Free Amination of C(sp3)–H Bonds Adjacent to Heteroatoms with Azoles: Synthesis of N-Alkylated Azoles
+
Z, Z' = C, O, S, N(Me)CO
Z Z'
H
Z Z'
NPhI(OAc)2 (1.0 equiv)
NH
Y
X
Ar
X = N, C Y = N, C
X
YArMetal-free
C–N bondHigh funtionality tolerance
25 examplesup to 96% yield
Letter
2432
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Synlett 2018, 29, 2437–2443DOI: 10.1055/s-0037-1610300
H.-S. HuangR. KongX.-A. ZhengW.-J. ChenS.-B. HanD.-Y. ZengS.-S. Gong*Q. Sun*Jiangxi Science and Technology Normal University, P. R. of China
Syn lett
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A Practical Method for Regioselective 5′-O-tert-Butyldimethylsilyl Deprotection of Persilylated Nucleosides by Methanolic Phosphomolybdic Acid
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Synlett 2018, 29, 2444–2448DOI: 10.1055/s-0037-1611062
X. TianY.-L. Ren*F. RenX. ChengS. ZhaoJ. Wang*Henan Normal University, P. R. of ChinaHenan University of Science and Technology, P. R. of China
as
Direct Conversion of Benzyl Ethers into Aryl Nitriles
Ar CH2OR Ar CN
NH4OAc
O2
Catalyst, 50 °C, 20 h
Letter
2444
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