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 W Kabalka

doi:10.1021/ol900669t

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

Org Lett. 2009 Jun 18;11(12):2647-9. doi: 10.1021/ol900669t.

Authors

Min-Liang Yao¹, Travis R Quick, Zhongzhi Wu, Michael P Quinn, George W Kabalka

Affiliation

¹ Department of Chemistry, The University of Tennessee, Knoxville, Tennessee 37996-1600, USA.

PMID: 19445487
DOI: 10.1021/ol900669t

Abstract

Alkoxide C-O 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.