Cobalt-Catalyzed Carbo- and Hydrocyanation of Alkynes via C-CN Bond Activation

被引：16

作者：

Wang, Chang-Sheng ^{[1
]}

Yu, Yongqi ^{[1
,2
]}

Sunada, Yusuke ^{[3
]}

Wang, Chen ^{[4
]}

Yoshikai, Naohiko ^{[1
,5
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

[2] Nanyang Normal Univ, Coll Chem & Pharmaceut Engn, Nanyang 473061, Henan, Peoples R China

[3] Univ Tokyo, Inst Ind Sci, Tokyo 1538505, Japan

[4] Shaoxing Univ, Zhejiang Key Lab Alternat Technol Fine Chem Proc, Shaoxing 312000, Peoples R China

[5] Tohoku Univ, Grad Sch Pharmaceut Sci, Sendai, Miyagi 9808578, Japan

来源：

ACS CATALYSIS | 2022年 / 12卷 / 07期

关键词：

C-C activation; cobalt; zinc; Lewis acids; carbocyanation; hydrocyanation; nitriles; alkynes; INTRAMOLECULAR ARYLCYANATION; 3,3-DISUBSTITUTED OXINDOLES; THEORETICAL-EXAMINATION; OXIDATIVE ADDITION; REACTION-MECHANISM; ALLYL CYANIDE; NICKEL; CLEAVAGE; PALLADIUM; CYANOESTERIFICATION;

D O I：

10.1021/acscatal.2c00181

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Cobalt-catalyzed carbo- and hydrocyanation reac-tions of alkynes via C-CN bond cleavage of organic cyanides arereported. A low-valent cobalt-diphosphine catalyst generated byreduction with Zn promotes the arylcyanation of alkynes withtrans-selectivity. By contrast, the addition of Zn(OTf)2to thiscatalytic system not only accelerates the transformation but alsoswitches the stereoselectivity, affordingcis-arylcyanation products.The present catalytic systems prove to be effective foralkenylcyanation using alkenyl cyanides as well as for transferhydrocyanation using propionitrile as the HCN surrogate. Experimental and computational studies on arylcyanation have beenperformed to gain insight into the reaction pathways, including the possible origin of the stereodivergence under cobalt and cobalt/zinc catalysis

引用

页码：4054 / 4066

页数：13

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