Synthesis of Unsymmetrical O-biphenols and O-binaphthols Via Silicon-tethered Pd-catalyzed C-H Arylation

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2010 Apr 29

PMID 20423110

Citations 7

Authors

Chunhui Huang

Vladimir Gevorgyan

Affiliations

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Abstract

A mild, practical, and efficient method for the synthesis of unsymmetrical o-biphenols (including o-phenol-naphthols and o-binaphthols) has been developed. Unsymmetrical bis-aryloxy silanes, which were readily prepared in a semi-one-pot fashion, underwent the Pd-catalyzed intramolecular arylation followed by a routine TBAF desilylation step to furnish valuable unsymmetrical biphenols without necessity of isolation of seven-membered intermediates. The excellent functional group tolerance allows for synthesis of a variety of functionalized o-biphenols and o-binaphthols from easily available staring materials.

Citing Articles

A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Sambiagio C, Schonbauer D, Blieck R, Dao-Huy T, Pototschnig G, Schaaf P Chem Soc Rev. 2018; 47(17):6603-6743.

PMID: 30033454 PMC: 6113863. DOI: 10.1039/c8cs00201k.

Silicon-Tethered Strategies for C-H Functionalization Reactions.

Parasram M, Gevorgyan V Acc Chem Res. 2017; 50(8):2038-2053.

PMID: 28771325 PMC: 5724575. DOI: 10.1021/acs.accounts.7b00306.

Studies on a biomimetic oxidative dimerization approach to the hibarimicins.

Romaine I, Sulikowski G Tetrahedron Lett. 2015; 56(23):3617-3619.

PMID: 26236055 PMC: 4518470. DOI: 10.1016/j.tetlet.2015.01.127.

Endo-selective Pd-catalyzed silyl methyl Heck reaction.

Parasram M, Iaroshenko V, Gevorgyan V J Am Chem Soc. 2014; 136(52):17926-9.

PMID: 25494921 PMC: 4291758. DOI: 10.1021/ja5104525.

The Pyridyldiisopropylsilyl Group: A Masked Functionality and Directing Group for Monoselective -Acyloxylation and -Halogenation Reactions of Arenes.

Huang C, Chernyak N, Dudnik A, Gevorgyan V Adv Synth Catal. 2013; 353(8).

PMID: 24363640 PMC: 3866842. DOI: 10.1002/adsc.201000975.

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