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

ABSTRACT: 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.

SUBMITTER: Molander GA

PROVIDER: S-EPMC3464102 | biostudies-literature | 2012 Sep

REPOSITORIES: biostudies-literature

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

Molander Gary A GA Trice Sarah L J SL Kennedy Steven M SM

Organic letters 20120904 18

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 met ...[more]

PMID: 22946672

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