TBDPS and Br-TBDPS protecting groups as efficient aryl group donors in Pd-catalyzed arylation of phenols and anilines

Chunhui Huang, Vladimir Gevorgyan

Research output: Contribution to journalArticle

67 Citations (Scopus)

Abstract

(Chemical Equation Presented) It is shown that the TBDPS protecting group can serve as an efficient phenyl group donor for o-bromophenols via Pd-catalyzed C-H arylation followed by a routine TBAF deprotection of the resulting silacycles. Employment of the newly designed Br-TBDPS protecting group in the same sequence allows for a facile introduction of a phenyl group at the ortho position of phenols and anilines. Alternatively, switching desilylation to oxidation in the last step allows the conversion of forming silacycles into valuable o-biphenols.

Original languageEnglish (US)
Pages (from-to)10844-10845
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number31
DOIs
StatePublished - Aug 12 2009
Externally publishedYes

Fingerprint

Aniline Compounds
Phenols
Aniline
Oxidation
2-bromophenol

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

TBDPS and Br-TBDPS protecting groups as efficient aryl group donors in Pd-catalyzed arylation of phenols and anilines. / Huang, Chunhui; Gevorgyan, Vladimir.

In: Journal of the American Chemical Society, Vol. 131, No. 31, 12.08.2009, p. 10844-10845.

Research output: Contribution to journalArticle

@article{544b4ce280cf40108dc8a15c4df3c390,
title = "TBDPS and Br-TBDPS protecting groups as efficient aryl group donors in Pd-catalyzed arylation of phenols and anilines",
abstract = "(Chemical Equation Presented) It is shown that the TBDPS protecting group can serve as an efficient phenyl group donor for o-bromophenols via Pd-catalyzed C-H arylation followed by a routine TBAF deprotection of the resulting silacycles. Employment of the newly designed Br-TBDPS protecting group in the same sequence allows for a facile introduction of a phenyl group at the ortho position of phenols and anilines. Alternatively, switching desilylation to oxidation in the last step allows the conversion of forming silacycles into valuable o-biphenols.",
author = "Chunhui Huang and Vladimir Gevorgyan",
year = "2009",
month = "8",
day = "12",
doi = "10.1021/ja904791y",
language = "English (US)",
volume = "131",
pages = "10844--10845",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "31",

}

TY - JOUR

T1 - TBDPS and Br-TBDPS protecting groups as efficient aryl group donors in Pd-catalyzed arylation of phenols and anilines

AU - Huang, Chunhui

AU - Gevorgyan, Vladimir

PY - 2009/8/12

Y1 - 2009/8/12

N2 - (Chemical Equation Presented) It is shown that the TBDPS protecting group can serve as an efficient phenyl group donor for o-bromophenols via Pd-catalyzed C-H arylation followed by a routine TBAF deprotection of the resulting silacycles. Employment of the newly designed Br-TBDPS protecting group in the same sequence allows for a facile introduction of a phenyl group at the ortho position of phenols and anilines. Alternatively, switching desilylation to oxidation in the last step allows the conversion of forming silacycles into valuable o-biphenols.

AB - (Chemical Equation Presented) It is shown that the TBDPS protecting group can serve as an efficient phenyl group donor for o-bromophenols via Pd-catalyzed C-H arylation followed by a routine TBAF deprotection of the resulting silacycles. Employment of the newly designed Br-TBDPS protecting group in the same sequence allows for a facile introduction of a phenyl group at the ortho position of phenols and anilines. Alternatively, switching desilylation to oxidation in the last step allows the conversion of forming silacycles into valuable o-biphenols.

UR - http://www.scopus.com/inward/record.url?scp=68249152000&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=68249152000&partnerID=8YFLogxK

U2 - 10.1021/ja904791y

DO - 10.1021/ja904791y

M3 - Article

C2 - 19722665

AN - SCOPUS:68249152000

VL - 131

SP - 10844

EP - 10845

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 31

ER -