Rhodium-Catalyzed Reductive Cleavage of Carbon-Cyano Bonds with Hydrosilane: A Catalytic Protocol for Removal of Cyano Groups

Rhodium-Catalyzed Reductive Cleavage of Carbon-Cyano Bonds with Hydrosilane: A Catalytic Protocol for Removal of Cyano Groups
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DOI:
10.1021/ja810142v
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发表时间:
2009-03-11
影响因子:
15
通讯作者:
Chatani, Naoto
Chatani, Naoto
中科院分区:
化学1区
文献类型:
--
作者:
Tobisu, Mamoru;Nakamura, Ryo;Chatani, Naoto

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使用氢硅烷作为温和还原剂开发了铑催化的碳-氰基还原断裂。多种亚硝酸盐,包括芳基、苄基和含B-氢的烷基氰化物都适用于该脱氰反应。该方法还可应用于有机合成;证明了使用苄基氰作为苄基阴离子等价物以及使用氰基作为可去除的邻位定向基团。
The rhodium-catalyzed reductive cleavage of carbon-cyano bonds is developed using hydrosilane as a mild reducing agent. A wide range of nitrites, including aryl, benzyl, and B-hydrogen containing alkyl cyanides are applicable to this decyanation reaction. The method can also be applied to organic synthesis; the use of benzyl cyanide as a benzyl anion equivalent and the use of a cyano group as a removable ortho-directing group are demonstrated.