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. 2014 Jan 3;79(1):365-78.
doi: 10.1021/jo402616w. Epub 2013 Dec 11.

A convergent, modular approach to functionalized 2,1-borazaronaphthalenes from 2-aminostyrenes and potassium organotrifluoroborates

Steven R Wisniewski  1 , Courtney L Guenther, O Andreea Argintaru, Gary A Molander
Affiliations

A convergent, modular approach to functionalized 2,1-borazaronaphthalenes from 2-aminostyrenes and potassium organotrifluoroborates

Steven R Wisniewski et al. J Org Chem. .

Abstract

Azaborines are an important class of compounds with applications in both medicinal chemistry and materials science. The first borazaronaphthalene, 2-chloro-2,1-borazaronaphthalene, was reported in 1959; however, access to more highly functionalized substructures has been limited because of the harsh reaction conditions required to displace the chloride on boron. A convergent approach has been developed to synthesize disubstituted 2,1-borazaronaphthalenes from N-substituted 2-aminostyrenes and potassium organotrifluoroborates, where the potassium organotrifluoroborate is converted to the active R-BX2 species (X = Cl or F) in situ by addition of a fluorophile. Starting from aryl-, heteroaryl-, alkynyl-, alkenyl-, and alkyltrifluoroborates, a library of highly functionalized 2,1-borazaronaphthalenes were synthesized in one step under mild, transition-metal-free conditions.

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Figures

Scheme 1
Scheme 1
Synthesis and Functionalization of 2,1-Borazaronaphthalenes.
Scheme 2
Scheme 2
Plausible Mechanism for the Synthesis of 2,1-Borazaronaphthalene.
Scheme 3
Scheme 3
Methods For Synthesizing Phenyldichloroborane.
See this image and copyright information in PMC

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