Halodeboronation of organotrifluoroborates using tetrabutylammonium tribromide or cesium triiodide

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

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Halodeboronation of organotrifluoroborates using commercially available tetrabutylammonium tribromide (TBATB) or cesium triiodide in aqueous medium is reported. The mild, transition metal-free method has proven to be tolerant of a wide range of functional groups. High regio- and chemoselectivity are observed. Two synthetic routes to (Z)-dibromoalkenes from alkynes, through stereodefined (Z)-2-bromoalkenyltrifluoroborates and (Z)-1,2-bis(boryl) alkenyltrifluoroborates, have been developed using the TBATB mediated bromodeboronation as the key step.

Original languageEnglish (US)
Pages (from-to)3738-3743
Number of pages6
JournalTetrahedron
Volume68
Issue number19
DOIs
StatePublished - May 13 2012
Externally publishedYes

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Cesium
Regioselectivity
Alkynes
Functional groups
Transition metals
Metals
tetrabutylammonium

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Halodeboronation of organotrifluoroborates using tetrabutylammonium tribromide or cesium triiodide. / Yao, Min Liang; Kabalka, George; Blevins, David; Reddy, Marepally Srinivasa; Yong, Li.

In: Tetrahedron, Vol. 68, No. 19, 13.05.2012, p. 3738-3743.

Research output: Contribution to journalArticle

Yao, Min Liang ; Kabalka, George ; Blevins, David ; Reddy, Marepally Srinivasa ; Yong, Li. / Halodeboronation of organotrifluoroborates using tetrabutylammonium tribromide or cesium triiodide. In: Tetrahedron. 2012 ; Vol. 68, No. 19. pp. 3738-3743.
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