cheminform abstract: synthesis of unsymmetrical o-biphenols and o-binaphthols via silicon-tethered...

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ChemInform 2010, 41, issue 40 © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim www.cheminform.wiley-vch.de Polyphenyl derivatives Q 0700 DOI: 10.1002/chin.201040081 Synthesis of Unsymmetrical o-Biphenols and o-Binaphthols via Silicon-Tethered Pd-Catalyzed C—H Arylation. — A practical and efficient synthesis of unsymmet- rical o-biphenol derivatives is presented. The method involves Pd-catalyzed intramo- lecular C—H arylation of bis(aryloxy)silanes followed by TBAF cleavage of the sili- con tether in the so formed dioxasilepanes [cf. (II)]. The method provides access to a wide range of o-biphenol, o-hydroxyphenylnaphthols as well as o-binaphthols in good yields. — (HUANG, C.; GEVORGYAN*, V.; Org. Lett. 12 (2010) 10, 2442-2445, DOI:10.1021/ol100924n ; Dep. Chem., Univ. Ill., Chicago, IL 60607, USA; Eng.) — Mischke 40- 081

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Page 1: ChemInform Abstract: Synthesis of Unsymmetrical o-Biphenols and o-Binaphthols via Silicon-Tethered Pd-Catalyzed C—H Arylation

www.cheminform.wiley-vch.de

Polyphenyl derivativesQ 0700 DOI: 10.1002/chin.201040081

Synthesis of Unsymmetrical o-Biphenols and o-Binaphthols via Silicon-Tethered Pd-Catalyzed C—H Arylation. — A practical and efficient synthesis of unsymmet-rical o-biphenol derivatives is presented. The method involves Pd-catalyzed intramo-lecular C—H arylation of bis(aryloxy)silanes followed by TBAF cleavage of the sili-con tether in the so formed dioxasilepanes [cf. (II)]. The method provides access to a wide range of o-biphenol, o-hydroxyphenylnaphthols as well as o-binaphthols in good yields. — (HUANG, C.; GEVORGYAN*, V.; Org. Lett. 12 (2010) 10, 2442-2445, DOI:10.1021/ol100924n ; Dep. Chem., Univ. Ill., Chicago, IL 60607, USA; Eng.) — Mischke

40- 081

ChemInform 2010, 41, issue 40 © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Page 2: ChemInform Abstract: Synthesis of Unsymmetrical o-Biphenols and o-Binaphthols via Silicon-Tethered Pd-Catalyzed C—H Arylation

www.cheminform.wiley-vch.de

ChemInform 2010, 41, issue 40 © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim