Copper-Catalyzed Regioselective Allylic Cyanation of Allylic Compounds with Trimethylsilyl Cyanide

被引：15
|
作者：
Munemori, Daisuke [1 ]
Tsuji, Hiroaki [1 ]
Uchida, Kenta [1 ]
Suzuki, Tomoaki [2 ]
Isa, Kazuki [2 ]
Minakawa, Maki [2 ]
Kawatsura, Motoi [2 ]
机构：
[1] Nihon Univ, Dept Chem, Coll Humanities & Sci, Setagaya Ku, Tokyo 1568550, Japan
[2] Tottori Univ, Grad Sch Engn, Dept Chem & Biotechnol, Tottori 6808552, Japan
来源：
SYNTHESIS-STUTTGART | 2014年 / 46卷 / 20期
关键词：
copper; catalysis; regioselectivity; radical reaction; nitriles; CONJUGATE ADDITION; PALLADIUM-COMPLEX; GRIGNARD-REAGENTS; EFFICIENT ROUTE; BOND FORMATION; ALKYLATION; SUBSTITUTION; CARBONATES; TRIFLUOROMETHYLATION; ESTERS;
D O I：
10.1055/s-0034-1378322
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The copper-catalyzed regioselective allylic cyanation of allylic compounds with trimethylsilyl cyanide (TMSCN) is described. Copper(I) iodide (CuI), copper(I) cyanide (CuCN) and copper(II) chloride (CuCl2) are shown to effectively catalyze the cyanation of various allylic substrates to afford the corresponding allylic cyanides in good yields and high regioselectivities. The reaction in the presence of 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (TEMPO) reveals that the cyanation proceeds via a radical pathway.
引用
收藏
页码：2747 / 2750
页数：4
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