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Ligand-Controlled Regioselective Dearomative Vicinal and Conjugate Hydroboration of Quinolines
Chao Hu1, Chen-Yan Cai1, Elizabeth S Barta2
1Department of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Blvd, Dallas, Texas 75390, United States.
Abstract:
A dearomative strategy to regioselectively modify arenes using a "diene" synthon within aromatic rings provides access to highly functionalized heterocycles from abundant aromatic feedstocks and represents an alternative synthetic approach besides traditional cross-coupling and C-H functionalization methodologies. In this study, we present an efficient method for selectively introducing boron onto quinolines through dearomative hydroboration using easily accessible and stable phosphine-ligated borane complexes. The vicinal 5,6- and conjugate 5,8-hydroborated products could be obtained regioselectively by modifying the phosphine ligand. Drawing inspiration from diverse organoboron transformations, these borane building blocks were diversified by a range of downstream functionalizations, providing modular pathways for the skeletal modifications of quinolines to access a variety of challenging functionalized heterocycles.
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