C(sp3 )−H Cyanation Promoted by Visible-Light Photoredox/Phosphate Hybrid Catalysis

Autor:	Kentaro Sakai, Takayuki Wakaki, Mio Kondo, Shigeyuki Masaoka, Kounosuke Oisaki, Takafumi Enomoto, Motomu Kanai
Rok vydání:	2018
Předmět:	Reaction mechanism 010405 organic chemistry Radical Organic Chemistry Photoredox catalysis General Chemistry Cyanation 010402 general chemistry Phosphate Photochemistry 01 natural sciences Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Nucleophile Phosphoric acid
Zdroj:	Chemistry - A European Journal. 24:8051-8055
ISSN:	0947-6539
DOI:	10.1002/chem.201801746
Popis:	Inspired by the reaction mechanism of photo-induced DNA cleavage in nature, a C(sp3 )-H cyanation reaction promoted by visible-light photoredox/phosphate hybrid catalysis was developed. Phosphate radicals, generated by one-electron photooxidation of phosphate salt, functioned as a hydrogen-atom-transfer catalyst to produce nucleophilic carbon radicals from C(sp3 )-H bonds with a high bond-dissociation energy. The resulting carbon radicals were trapped by a cyano radical source (TsCN) to produce the C-H cyanation products. Due to the high functional-group tolerance and versatility of the cyano group, the reaction will be useful for realizing streamlined building block syntheses and late-stage functionalization of drug-like molecules.
Databáze:	OpenAIRE
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