Titanium(IV) halide mediated coupling of alkoxides and alkynes: An efficient and stereoselective route to trisubstituted (E)-alkenyl halides

Min Liang Yao, Travis R. Quick, Zhongzhi Wu, Michael P. Quinn, George Kabalka

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Alkoxide C - 0 bond cleavage occurs readily at room temperature in the presence of titanium(IV) halide. Capture of the resultant carbocation by alkynes provides an efficient route to trisubstituted (E)-alkenyl halides with high stereoselectivity.

Original languageEnglish (US)
Pages (from-to)2647-2649
Number of pages3
JournalOrganic Letters
Volume11
Issue number12
DOIs
StatePublished - Jun 18 2009

Fingerprint

Stereoselectivity
Alkynes
alkoxides
alkynes
Titanium
halides
titanium
routes
Temperature
cleavage
room temperature

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Titanium(IV) halide mediated coupling of alkoxides and alkynes : An efficient and stereoselective route to trisubstituted (E)-alkenyl halides. / Yao, Min Liang; Quick, Travis R.; Wu, Zhongzhi; Quinn, Michael P.; Kabalka, George.

In: Organic Letters, Vol. 11, No. 12, 18.06.2009, p. 2647-2649.

Research output: Contribution to journalArticle

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abstract = "Alkoxide C - 0 bond cleavage occurs readily at room temperature in the presence of titanium(IV) halide. Capture of the resultant carbocation by alkynes provides an efficient route to trisubstituted (E)-alkenyl halides with high stereoselectivity.",
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