Related Experiment Video
Updated: Sep 18, 2025
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Photocatalytic Decyanative Radical Addition Based on Cyano Group Transfer Mediated by Amine-Ligated Boryl Radicals
Yuto Yoshida1, Waka Okada1, Kazutake Takada1
1Department of Life Science and Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
None:
Herein, we describe a photocatalytic strategy for decyanative hydrofunctionalization of styrenes with α-heteroatom-substituted acetonitriles. This strategy facilitates the generation of α-heteroatom methyl radicals from acetonitriles through cyano group transfer (CGT) enabled by amine-ligated boryl radicals. The broad applicability of this method is demonstrated by its successful application in late-stage functionalization of bioactive compounds. Combined experimental and computational studies suggest that the strong nucleophilic character of amine-ligated boryl radical is beneficial in facilitating the CGT process.
More Related Videos
Related Concept Videos
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism
Radical Formation: Addition
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
Cycloaddition Reactions: Overview
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

