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Synthesis of 2,3‐Disubstituted 1,4‐Naphthoquinones via Metal‐Free C(sp2)‐H Functionalization Followed by Suzuki Cross‐Coupling Reactions
Author(s) -
Borah Ashwini,
Sharma Abhilash,
Hazarika Hemanta,
Gogoi Pranjal
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201702404
Subject(s) - chemistry , toluene , benzaldehyde , suzuki reaction , combinatorial chemistry , surface modification , coupling reaction , organic chemistry , catalysis , palladium
A synthetic strategy has been developed for the synthesis of 2,3‐disubstituted‐1,4‐naphthoquinones. This synthetic protocol consists of metal‐free tert‐Butyl hydroperoxide (TBHP)‐mediated oxidative benzoylation followed by Pd‐catalyzed Suzuki‐cross coupling reactions. Benzaldehyde, benzylalcohol and toluene were efficiently used as benzoyl radical source for the benzoylation of 1,4‐naphthoquinones. By this protocol, a wide range of 1,4‐naphthoquinones with different substitution patterns were efficiently prepared in a sequential way with good to excellent yields.