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Denitrogenative Suzuki and carbonylative Suzuki coupling reactions of benzotriazoles with boronic acids.

ABSTRACT: Unprecedented palladium-catalyzed denitrogenative Suzuki and carbonylative Suzuki coupling reactions of benzotriazoles with boronic acids have been realized, which afforded structurally diverse ortho-amino-substituted biaryl and biaryl ketone derivatives. The key to this success is due to the development of a rationally designed strategy to achieve the ring opening of benzotriazoles with a synergistic activating-stabilizing effect, which enables the in situ generation of the corresponding ortho-amino-arenediazonium species. The present work opens up a new avenue to utilize benzotriazoles as synthetic equivalents of ortho-amino-arenediazoniums, which otherwise could not be directly accessed by existing synthetic methods.

SUBMITTER: Wang Y

PROVIDER: S-EPMC5578364 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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Denitrogenative Suzuki and carbonylative Suzuki coupling reactions of benzotriazoles with boronic acids.

Wang Yuanhao Y Wu Yunfei Y Li Yuanhe Y Tang Yefeng Y

Chemical science 20170315 5

Unprecedented palladium-catalyzed denitrogenative Suzuki and carbonylative Suzuki coupling reactions of benzotriazoles with boronic acids have been realized, which afforded structurally diverse <i>ortho</i>-amino-substituted biaryl and biaryl ketone derivatives. The key to this success is due to the development of a rationally designed strategy to achieve the ring opening of benzotriazoles with a synergistic activating-stabilizing effect, which enables the <i>in situ</i> generation of the corres ...[more]

PMID: 28966777

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