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Photoredox Catalysis Enables Access to N-Functionalized 2,1-Borazaronaphthalenes.

ABSTRACT: The synthesis and utilization of a class of 2,1-borazaronaphthyltrifluoroborate reagents that provide a general solution to the challenge of N-functionalization of the 2,1-borazaronaphthalene core is described. By adorning the nitrogen of this core with a trifluoroboratomethyl unit, a suite of odd-electron processes can be executed, installing motifs that would otherwise be inaccessible using a two-electron approach. In addition, this process enables rapid annulation, furnishing a heretofore unknown polycyclic B-N species.

SUBMITTER: Wang X

PROVIDER: S-EPMC6490172 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Photoredox Catalysis Enables Access to N-Functionalized 2,1-Borazaronaphthalenes.

Wang Xie X Davies Geraint H M GHM Koschitzky Adriel A Wisniewski Steven R SR Kelly Christopher B CB Molander Gary A GA

Organic letters 20190327 8

The synthesis and utilization of a class of 2,1-borazaronaphthyltrifluoroborate reagents that provide a general solution to the challenge of N-functionalization of the 2,1-borazaronaphthalene core is described. By adorning the nitrogen of this core with a trifluoroboratomethyl unit, a suite of odd-electron processes can be executed, installing motifs that would otherwise be inaccessible using a two-electron approach. In addition, this process enables rapid annulation, furnishing a heretofore unk ...[more]

PMID: 30916973

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