Z-Selective Olefin Synthesis via Iron-Catalyzed Reductive Coupling of Alkyl Halides with Terminal Arylalkynes

Selective catalytic synthesis of Z-olefins has been challenging. Here we describe a method to produce 1,2-disubstituted olefins in high Z selectivity via reductive cross-coupling of alkyl halides with terminal arylalkynes. The method employs inexpensive and nontoxic catalyst (iron(II) bromide) and reductant (zinc). The substrate scope encompasses primary, secondary, and tertiary alkyl halides, and the reaction tolerates a large number of functional groups. The utility of the method is demonstrated in the synthesis of several pharmaceutically relevant molecules. Mechanistic study suggests that the reaction proceeds through an iron-catalyzed anti-selective carbozincation pathway.


Published in:
Journal Of The American Chemical Society, 137, 15, 4932-4935
Year:
2015
Publisher:
Washington, American Chemical Society
ISSN:
0002-7863
Laboratories:




 Record created 2015-05-29, last modified 2018-09-13

Publisher's version:
Download fulltextPDF
SI:
Download fulltextPDF
Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)