Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 28, Pages 8932-8935Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b05879
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Funding
- NIH NIGMS [R01-GM094541]
- NSF [CHE-1361618]
- Camille Dreyfus Teacher-Scholar Awards Program
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1361618] Funding Source: National Science Foundation
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The compatibility of the Negishi cross-coupling reaction with the versatile B-Cl functionality has been demonstrated in the context of late-stage functionalization of 1,2-azaborines. Alkyl-, aryl-, and alkenylzinc reagents have been utilized for the functionalization of the triply orthogonal precursor 3-bromo-1-(tert-butyldimethyl-sily1)-2-chloro-1,2-dihydro-1,2-azaborine (2) to furnish new 2,3-substituted monocyclic 1,2-azaborines. This methodology has enabled the synthesis of previously elusive BN-naphthalene and BN-indenyl structures from a common intermediate.
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