Halogenation/Cyanation vs. Cyanation/Halogenation of Alkenes Using ICN and BrCN-Reference-Cited by-同舟云学术

Halogenation/Cyanation vs. Cyanation/Halogenation of Alkenes Using ICN and BrCN

Published:2023-07-27 Issue:19 Volume:365 Page:3247-3252
ISSN:1615-4150
Container-title:Advanced Synthesis & Catalysis
language:en
Short-container-title:Adv Synth Catal

Author:

Furusawa Ikumi¹,Suzuki Takumi¹,Yu Yan¹,Arai Takayoshi¹^ORCID

Affiliation:

1. Soft Molecular Activation Research Center (SMARC) Chiba Iodine Research Innovation Center (CIRIC) Department of Chemistry Graduate School of Science Chiba University 1-33 Yayoi Inage Chiba 263-8522 Japan

Abstract

AbstractIn a tris(pentafluorophenyl)borane [B(C6F5)3]‐catalyzed reaction of alkenes with cyanogen halides (XCN), BrCN proceeds in a cyanation/bromination manner, in which a cationic CN character is realized. The reaction using ICN switched the mode to iodination/cyanation for enamide substrates and electron‐enriched styrenes. The origin of the iodination/cyanation is the B(C6F5)3‐enhanced σ‐hole generated on ICN.

Publisher

Wiley

Subject

Organic Chemistry,Catalysis

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.202300458

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