Nickel-Catalyzed Cyanation of Aryl Halides and Hydrocyanation of Alkynes via C-CN Bond Cleavage and Cyano Transfer

被引:73
作者
Chen, Hui [1 ]
Sun, Shuhao [1 ]
Liu, Yahu A. [2 ]
Liao, Xuebin [1 ]
机构
[1] Tsinghua Univ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing Adv Innovat Ctr Struct Biol, Sch Pharmaceut Sci,Minist Educ, Beijing 100084, Peoples R China
[2] Novartis Res Fdn GNF, Genom Inst, Discovery Chem, San Diego, CA 92121 USA
关键词
nickel catalysis; cyanation; hydrocyanation; C-CN bond cleavage; Z/E selectivity; Markovnikov addition; CARBON-CARBON BONDS; H CYANATION; DECARBONYLATIVE CYANATION; CONJUGATE CYANATION; OXIDATIVE CYANATION; STRECKER REACTION; PALLADIUM; MILD; ACTIVATION; PHOTOREDOX;
D O I
10.1021/acscatal.9b04586
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
We report nickel-catalyzed cyanation and hydrocyanation methods to prepare aryl nitriles and vinyl nitriles from aryl halides and alkynes, respectively. Using inexpensive and nontoxic 4-cyanopyridine N-oxide as the cyano shuttle, the methods provide an efficient approach to prepare aryl cyanides and vinyl nitriles under mild and operationally simple reaction conditions with a broad range of functional group tolerances. In hydrocyanation of alkynes, the method demonstrated good regioselectivity, producing predominantly E- or Z-alkenyl nitriles in a controlled manner and exclusively Markovnikov vinyl nitriles when internal diaryl alkynes and terminal alkynes were applied as the substrates, respectively. The preliminary mechanistic investigation indicated that the C-CN bond cleavage process is promoted by oxidative addition to the nickel(I) complex in the cyanation of aryl halides, and further studies via a series of deuterium exchange experiments indicated that water serves as the hydrogen source for the hydrocyanation of alkynes.
引用
收藏
页码:1397 / 1405
页数:17
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