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Org Lett. 2012 Sep 21;14(18):4814-7. Epub 2012 Sep 4.

Palladium-catalyzed borylation of aryl and heteroaryl halides utilizing tetrakis(dimethylamino)diboron: one step greener.

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  • 1Roy and Diana Vagelos Laboratories and Penn/Merck Laboratory for High Throughput Experimentation, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.


The palladium-catalyzed borylation of aryl and heteroaryl halides with a novel borylating agent, tetrakis(dimethylamino)diboron [(Me(2)N)(2)B-B(NMe(2))(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 (B(2)Pin(2)), the new method represents a more atom-economical and efficient approach to current borylation methods.

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