Palladium-Catalyzed Borylation of Aryl and Heteroaryl Halides Utilizing Tetrakis(dimethylamino)diboron: One Step Greener

The palladium-catalyzed borylation of aryl and heteroaryl halides with a novel borylating agent, tetrakis(dimethylamino)diboron [(Me2N)2B–B(NMe2)2], is reported. The method is complementary to the previously reported method utilizing bis-boronic acid (BBA) in that certain substrates perform better u...

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Bibliographic Details
Published in:Organic letters 2012-09, Vol.14 (18), p.4814-4817
Main Authors: Molander, Gary A, Trice, Sarah L. J, Kennedy, Steven M
Format: Article
Language:English
Subjects:
Boron Compounds - chemical synthesis
Boron Compounds - chemistry
Catalysis
Combinatorial Chemistry Techniques
Hydrocarbons, Halogenated - chemical synthesis
Hydrocarbons, Halogenated - chemistry
Molecular Structure
Palladium - chemistry
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Summary:The palladium-catalyzed borylation of aryl and heteroaryl halides with a novel borylating agent, tetrakis(dimethylamino)diboron [(Me2N)2B–B(NMe2)2], is reported. The method is complementary to the previously reported method utilizing bis-boronic acid (BBA) in that certain substrates perform better under one set of optimized reaction conditions than the other. Because tetrakis(dimethylamino)diboron is the synthetic precursor to both BBA and bis(pinacolato)diboron (B2Pin2), the new method represents a more atom-economical and efficient approach to current borylation methods.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol302124j