A Metallaphotoredox Strategy for the Cross-Electrophile Coupling of α-Chloro Carbonyls with Aryl Halides.
Angew Chem Int Ed Engl
; 58(41): 14584-14588, 2019 10 07.
Article
in En
| MEDLINE
| ID: mdl-31410960
Here, we demonstrate that a metallaphotoredox-catalyzed cross-electrophile coupling mechanism provides a unified method for the α-arylation of diverse activated alkyl chlorides, including α-chloroketones, α-chloroesters, α-chloroamides, α-chlorocarboxylic acids, and benzylic chlorides. This strategy, which is effective for a wide variety of aryl bromide coupling partners, is predicated upon a halogen atom abstraction/nickel radical-capture mechanism that is generically successful across an extensive range of carbonyl substrates. The construction and use of arylacetic acid products have further enabled two-step protocols for the delivery of valuable building blocks for medicinal chemistry, such as aryldifluoromethyl and diarylmethane motifs.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Hydrocarbons, Cyclic
/
Metals
Language:
En
Journal:
Angew Chem Int Ed Engl
Year:
2019
Document type:
Article
Affiliation country:
United States
Country of publication:
Germany