Stereoselective Synthesis of Trisubstituted Alkenes through Sequential Iron-Catalyzed Reductive anti-Carbozincation of Terminal Alkynes and Base-Metal-Catalyzed Negishi CrossCoupling

The stereoselective synthesis of trisubstituted alkenes is challenging. Here, we show that an iron-catalyzed anti-selective carbozincation of terminal alkynes can be combined with a base-metal-catalyzed cross coupling to prepare trisubstituted alkenes in a one-pot reaction and with high regio- and stereocontrol. Cu-, Ni-, and Co-based catalytic systems are developed for the coupling of sp(-), sp(2)-, and sp(-) hybridized carbon electrophiles, respectively. The method encompasses a large substrate scope, as various alkynyl, aryl, alkenyl, acyl, and alkyl halides are suitable coupling partners. Compared with conventional carbometalation reactions of alkynes, the current method avoids pre-made organometallic reagents and has a distinct stereoselectivity.


Published in:
Chemistry - A European Journal, 21, 50, 18439-18444
Year:
2015
Publisher:
Wiley-Blackwell
ISSN:
0947-6539
Laboratories:




 Record created 2016-01-22, last modified 2018-03-17

Postprint:
Download fulltextPDF
n/a:
Download fulltextPDF
Rate this document:

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