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Unlocking Mizoroki–Heck-Type Reactions of Aryl Cyanides Using Transfer Hydrocyanation as a Turnover-Enabling Step

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Fang,  Xianjie
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Yu,  Peng
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Prina Cerai,  Gabriele
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Morandi,  Bill
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fang, X., Yu, P., Prina Cerai, G., & Morandi, B. (2016). Unlocking Mizoroki–Heck-Type Reactions of Aryl Cyanides Using Transfer Hydrocyanation as a Turnover-Enabling Step. Chemistry – A European Journal, 22(44), 15629-15633. doi:10.1002/chem.201604061.


Cite as: https://hdl.handle.net/11858/00-001M-0000-002B-A628-B
Abstract
A new transfer hydrofunctionalization strategy to turnover H-MII-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.