Nickel-Catalyzed Markovnikov Transfer Hydrocyanation in the Absence of Lewis Acid

被引:15
|
作者
Frye, Nils L. [1 ]
Bhunia, Anup [1 ]
Studer, Armido [1 ]
机构
[1] Westfalische Wilhelms Univ, Organ Chem Inst, D-48149 Munster, Germany
关键词
PHOSPHINE-PHOSPHITE LIGANDS; CHEMISTRY; OLEFINS; STEREOCHEMISTRY; INTERCONVERSION; DERIVATIVES; MECHANISM; NITRILES; ALKENES;
D O I
10.1021/acs.orglett.0c01454
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hydrocyanation in the absence of toxic HCN gas is highly desirable. Addressing that challenge, transition-metal-catalyzed transfer hydrocyanation using safe HCN precursors has been developed, but these reagents generally require a Lewis acid for activation, and the control of regioselectivity often remains problematic. In this Letter, a Ni-catalyzed highly Markovnikov-selective transfer hydrocyanation that operates in the absence of any Lewis acid is reported. The readily prepared pro-aromatic 1-isopropylcyclohexa-2,5-diene-1-carbonitrile is used as the HCN source, and the reaction shows a broad substrate scope and high functional group tolerance. Terminal styrene derivatives, dienes, and internal alkynes are converted with good to excellent selectivities. Mechanistic studies provide insights into the origin of the regioselectivity.
引用
收藏
页码:4456 / 4460
页数:5
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