Formal 1,1-Hydrocyanation\nReaction of Alkynyl Halides\nwith Isocyanides Enabled by Dual Nickel/Base Catalysis Relay

We herein describe a formal 1,1-hydrocyanation reaction\nof alkynyl\nhalides with isocyanides enabled by a dual nickel/base catalysis relay. <i>tert</i>-Butyl isocyanide serves as a “HCN” precursor\nthat is introduced to the α-position of alkynyl halides, and\nthe halogen atom is moved to the β-position. As a result, a\nseries of (<i>Z</i>)-3-bromo/iodo acrylonitrile derivatives\ncould be obtained in moderate yields. Mechanistic experiments were\ncarried out, and the collective data could support our proposal of\nthe mechanism details.

Publication Details

Journal
Figshare
Published
2024-12-04
DOI
https://doi.org/10.1021/acs.orglett.4c03901.s001
Primary Topic
Catalytic C–H Functionalization Methods
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article
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article

Formal 1,1-Hydrocyanation\nReaction of Alkynyl Halides\nwith Isocyanides Enabled by Dual Nickel/Base Catalysis Relay

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Catalytic C–H Functionalization Methods
article

Formal 1,1-Hydrocyanation\nReaction of Alkynyl Halides\nwith Isocyanides Enabled by Dual Nickel/Base Catalysis Relay

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Abstract

We herein describe a formal 1,1-hydrocyanation reaction\nof alkynyl\nhalides with isocyanides enabled by a dual nickel/base catalysis relay. <i>tert</i>-Butyl isocyanide serves as a “HCN” precursor\nthat is introduced to the α-position of alkynyl halides, and\nthe halogen atom is moved to the β-position. As a result, a\nseries of (<i>Z</i>)-3-bromo/iodo acrylonitrile derivatives\ncould be obtained in moderate yields. Mechanistic experiments were\ncarried out, and the collective data could support our proposal of\nthe mechanism details.

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Catalytic C–H Functionalization Methods
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Formal 1,1-Hydrocyanation\nReaction of Alkynyl Halides\nwith Isocyanides Enabled by Dual Nickel/Base Catalysis Relay · Figshare (2024) | TGRS Research Map | TGRS