期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 138, 期 14, 页码 4860-4868出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b00819
关键词
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资金
- Academy of Finland [139550, 276586]
- Hungarian Scientific Research Fund (OTKA) [K-115660]
- Academy of Finland (AKA) [276586, 139550, 139550, 276586] Funding Source: Academy of Finland (AKA)
C-H borylation is a powerful and atom-efficient method for converting affordable and abundant chemicals into versatile organic reagents used in the production of fine chemicals and functional materials. Herein we report a facile C-H borylation of aromatic and olefinic C-H bonds with 2-aminophenylboranes. Computational and experimental studies reveal that the metal-free C-H insertion proceeds via a frustrated Lewis pair mechanism involving heterolytic splitting of the C-H bond by cooperative action of the amine and boryl groups. The adapted geometry of the reactive B and N centers results in an unprecedentently low kinetic barrier for both insertion into the sp(2)-C-H bond and intramoleculai protonation of the sp(2)-C-B bond in 2-ammoniophenyl(aryl)- or -(alkenyl)borates. This common reactivity pattern serves as a platform for various catalytic reactions such as C-H borylation and hydrogenation of alkynes. In particular, we demonstrate that simple 2-aminopyridinium salts efficiently catalyze the C-H borylation of hetarenes with catecholborane. This reaction is presumably mediated by a borenium species isoelectronic to 2-aminophenylboranes.
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