Selective Carbonyl−C(sp 3 ) Bond Cleavage To Construct Ynamides, Ynoates, and Ynones by Photoredox Catalysis | Zendy

Jia Kunfang | Zendy; Pan Yue | Zendy; Chen Yiyun | Zendy

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Selective Carbonyl−C(sp 3 ) Bond Cleavage To Construct Ynamides, Ynoates, and Ynones by Photoredox Catalysis

Author(s) -

Jia Kunfang,

Pan Yue,

Chen Yiyun

Publication year - 2017

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201611897

Subject(s) - chemistry , ketone , bond cleavage , photoredox catalysis , chemoselectivity , catalysis , medicinal chemistry , alkynylation , alkoxy group , triple bond , cleavage (geology) , reagent , combinatorial chemistry , organic chemistry , double bond , alkyl , photocatalysis , geotechnical engineering , fracture (geology) , engineering

Carbon–carbon bond cleavage/functionalization is synthetically valuable, and selective carbonyl−C(sp 3 ) bond cleavage/alkynylation presents a new perspective in constructing ynamides, ynoates, and ynones. Reported here is the first alkoxyl‐radical‐enabled carbonyl−C(sp 3 ) bond cleavage/alkynylation reaction by photoredox catalysis. The use of novel cyclic iodine(III) reagents are essential for β‐carbonyl alkoxyl radical generation from β‐carbonyl alcohols, including alcohols with high redox potential ( E p ox >2.2 V vs. SCE in MeCN). β‐Amide, β‐ester, and β‐ketone alcohols yield ynamides, ynoates, and ynones, respectively, for the first time, with excellent regio‐ and chemoselectivity under mild reaction conditions.

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