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Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4].

ABSTRACT: Arylboronic acids are gaining increased importance as reagents and target structures in a variety of useful applications. Recently, the palladium-catalyzed synthesis of arylboronic acids employing the atom-economical tetrahydroxydiboron (BBA) reagent has been reported. The high cost associated with palladium, combined with several limitations of both palladium- and copper-catalyzed processes, prompted us to develop an alternative method. Thus, the nickel-catalyzed borylation of aryl and heteroaryl halides and pseudohalides using tetrahydroxydiboron (BBA) has been formulated. The reaction proved to be widely functional group tolerant and applicable to a number of heterocyclic systems. To the best of our knowledge, the examples presented here represent the only effective Ni-catalyzed Miyaura borylations conducted at room temperature.

SUBMITTER: Molander GA

PROVIDER: S-EPMC3740274 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4].

Molander Gary A GA Cavalcanti Livia N LN García-García Carolina C

The Journal of organic chemistry 20130618 13

Arylboronic acids are gaining increased importance as reagents and target structures in a variety of useful applications. Recently, the palladium-catalyzed synthesis of arylboronic acids employing the atom-economical tetrahydroxydiboron (BBA) reagent has been reported. The high cost associated with palladium, combined with several limitations of both palladium- and copper-catalyzed processes, prompted us to develop an alternative method. Thus, the nickel-catalyzed borylation of aryl and heteroar ...[more]

PMID: 23777538

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