Premium
Catalytic Cyanation of Carbon‐Carbon Triple Bonds Through a Three‐Component Cross‐Coupling Reaction under Nickel Catalysis
Author(s) -
Yang Xiaofei,
Arai Shigeru,
Nishida Atsushi
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300553
Subject(s) - chemistry , cyanation , allene , triple bond , catalysis , nickel , coupling reaction , reinforced carbon–carbon , medicinal chemistry , carbon fibers , stereochemistry , photochemistry , double bond , organic chemistry , materials science , composite number , composite material
A nickel‐catalyzed three‐component coupling reaction through cyanation of a carbon‐carbon triple bond is described. A nickel(0) complex effectively catalyzes a sequential coupling reaction between allenes, alkynes and hydrogen cyanide from acetone cyanohydrin in a highly regio‐ and stereoselective fashion. The trigger for this reaction is hydronickelation to allenes. The initial hydride attack predominantly occurs at the central carbon of the allene to give a π‐allylnickel(II) species. Subsequent syn ‐carbometalation connects a β‐carbon of alkynoates and a less‐hindered carbon of the allylnickel(II) species, and the corresponding cyanoalkenes are obtained as a single stereoisomer without any another organometallic reagents as a coupling partner.