Metal-free borylation of electron-rich aryl (pseudo)halides under continuous-flow photolytic conditions
Literature Information
Publication Date
2016-05-13
DOI
10.1039/C6QO00109B
Impact Factor
5.281
Authors
Kai Chen, Man Sing Cheung, Zhenyang Lin, Pengfei Li
View Original
Abstract
A metal-free borylation reaction of electron-rich aryl chlorides, fluorides, mesylates and phosphates under continuous-flow photolytic conditions is reported. The flow setup was designed to facilitate this process efficiently in comparison with the batch mode. Owing to its unique chemical selectivity, mild reaction conditions, good functional group tolerance and substrate scope, this reaction adds a complementary protocol to the current synthetic methods for boronic acid derivatives. The proposed reaction mechanism involves a photolytically generated triplet aryl cation, and DFT calculations suggest that the borylation product is formed in an anion-mediated single step process passing a minimum energy crossing point.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
N1,N1-Bis(4-aminophenyl)benzene-1,4-diamine trihydrochloride
CAS Number:
114254-48-7
Molecular Formula:
C18H21Cl3N4
5,5',5''-(((2,4,6-Trimethylbenzene-1,3,5-triyl)tris(methylene))tris(oxy))triisophthalic acid
CAS Number:
1159974-70-5
Molecular Formula:
C36H30O15
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