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Photocatalytic C( sp 3 )−H Activation towards α‐methylenation of Ketones using MeOH as 1 C Source Steering Reagent
Author(s) -
Verma Fooleswar,
Shukla Prashant,
Bhardiya Smita R.,
Singh Manorama,
Rai Ankita,
Rai Vijai K.
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801431
Subject(s) - chemistry , methanol , reagent , substrate (aquarium) , photocatalysis , catalysis , formaldehyde , solvent , aryl , yield (engineering) , aldol reaction , aldehyde , methylene , visible spectrum , photochemistry , organic chemistry , combinatorial chemistry , oceanography , alkyl , materials science , optoelectronics , physics , metallurgy , geology
Unprecedented direct access to terminal enones via α‐methylenation of aryl ketones to form C=C bond is achieved under visible‐light conditions using methanol as one carbon source substrate and solvent as well. The reaction involves Cu@g‐C 3 N 4 ‐catalysed in situ oxidation of methanol into formaldehyde followed by dehydrative cross aldol type reaction. Various aryl ketones react efficiently with MeOH, producing α,β‐unsaturated carbonyl compounds only in 4–8 h at room temperature in excellent yield (84–97%). Operational simplicity, wide substrate scope, ambient reaction conditions, visible‐light photocatalysis and novel application of MeOH as methylene donor substrate are the salient features making the envisaged protocol mild, efficient and green alternative to the existing methods for synthesis of such fine chemicals.