Catalytic 1,2-Dicyanation of Alkynes by Palladium(II) under Aerobic Conditions

被引：27
作者：
Arai, Shigeru [1 ]
Sato, Takashi [1 ]
Nishida, Atsushi [1 ]
机构：
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 11-12期
关键词：
alkynes; cyanation; oxygen; palladium; CARBON TRIPLE BONDS; TRIMETHYLSILYL CYANIDE; STEREOSELECTIVE SYNTHESIS; TERMINAL ACETYLENES; OXIDATIVE ADDITION; C-C; NICKEL; ARYLCYANATION; ARYLACETYLENES; CYANATION;
D O I：
10.1002/adsc.200900334
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A stereoselective 1,2-dicyanation of various alkynes in the presence of trimethylsilyl cyanide (TMSCN) by palladium(II) catalysis under aerobic conditions is investigated. This reaction includes two cyanation pathways, syn- and anti-cyanopalladation to alkynes that are activated by Pd(II). High syn-selectivity was observed in the reaction using terminal alkynes that have bulky substituents at a propargyl position and aliphatic internal alkynes. Furthermore, a dramatic acceleration was observed with substrates having an N-arenesulfonyl functionality at a propargyl position, this indicates that both sulfoxide and carbon-carbon triple bond act as Lewis bases to Pd(II).
引用
收藏
页码：1897 / 1904
页数：8
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