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Unlocking Mizoroki–Heck‐Type Reactions of Aryl Cyanides Using Transfer Hydrocyanation as a Turnover‐Enabling Step
Author(s) -
Fang Xianjie,
Yu Peng,
Prina Cerai Gabriele,
Morandi Bill
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604061
Subject(s) - hydrocyanation , chemistry , aryl , intermolecular force , alkyne , reactivity (psychology) , catalysis , heck reaction , catalytic cycle , organic chemistry , combinatorial chemistry , palladium , molecule , alkyl , medicine , alternative medicine , pathology
A new transfer hydrofunctionalization strategy to turnover H‐M II ‐X complexes has enabled both intra‐ and intermolecular Mizoroki–Heck (MH)‐type reactions of aryl cyanides that are challenging to realize under traditional, basic conditions. Initially, a cascade carbonickelation/MH reaction of 2‐cyanostyrenes was achieved using a key alkyne transfer hydrocyanation step. Mechanistic experiments supported the proposed catalytic cycle, including the turnover‐enabling transfer hydrocyanation step. The reactivity was then extended to the intermolecular MH reaction of benzonitriles and styrenes.