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Synthesis of unsymmetrical o-biphenols and o-binaphthols via silicon-tethered Pd-catalyzed C-H arylation.

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.

SUBMITTER: Huang C 

PROVIDER: S-EPMC2873232 | biostudies-literature | 2010 May

REPOSITORIES: biostudies-literature

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Synthesis of unsymmetrical o-biphenols and o-binaphthols via silicon-tethered Pd-catalyzed C-H arylation.

Huang Chunhui C   Gevorgyan Vladimir V  

Organic letters 20100501 10

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 f  ...[more]

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