Chemoselective bromodeboronation of organotrifluoroborates using tetrabutylammonium tribromide: Application in (Z)-dibromoalkene syntheses

Min Liang Yao, Marepally Srinivasa Reddy, Yong Li, Ingrid Walfish, David Blevins, George Kabalka

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

(Chemical Equation Presented) Tetrabutylammonlum trlbromlde (TBATB) has been found to be a unique bromodeboronatlon reagent for organotrlf luoroborates. When compared to previously reported bromodeboronatlon methods, the mild and metal-free reaction conditions tolerate a wider range of functional groups. High reglo- and chemoselectlvlty are observed In the presence of both unsaturated carbon-carbon bonds and aldehyde functional groups. An efficient synthetic route to (Z)-dlbromoalkenes from terminal alkynes has been developed using the TBATB-medlated bromodeboronatlon as a key step.

Original languageEnglish (US)
Pages (from-to)700-703
Number of pages4
JournalOrganic letters
Volume12
Issue number4
DOIs
StatePublished - Feb 19 2010
Externally publishedYes

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Functional groups
Carbon
Alkynes
carbon
alkynes
synthesis
aldehydes
Aldehydes
reagents
Metals
routes
metals
tetrabutylammonium

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Chemoselective bromodeboronation of organotrifluoroborates using tetrabutylammonium tribromide : Application in (Z)-dibromoalkene syntheses. / Yao, Min Liang; Reddy, Marepally Srinivasa; Li, Yong; Walfish, Ingrid; Blevins, David; Kabalka, George.

In: Organic letters, Vol. 12, No. 4, 19.02.2010, p. 700-703.

Research output: Contribution to journalArticle

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AU - Reddy, Marepally Srinivasa

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AU - Kabalka, George

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