Boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with silylborane and an alkoxy base: expanded scope and mechanistic studies† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c5sc00384a Click here for additional data file.

نویسندگان

  • Eiji Yamamoto
  • Satoshi Ukigai
  • Hajime Ito
چکیده

A transition-metal-free method has been developed for the boryl substitution of functionalized aryl-, heteroaryland alkenyl halides with a silylborane in the presence of an alkali-metal alkoxide. The basemediated boryl substitution of organohalides with a silylborane was recently reported to provide the corresponding borylated products in good to high yields, and exhibit good functional group compatibility and high tolerance to steric hindrance. In this study, the scope of this transformation has been extended significantly to include a wide variety of functionalized aryl-, heteroaryland alkenyl halides. In particular, the boryl substitution of (E)and (Z)-alkenyl halides proceeded smoothly to afford the corresponding alkenyl boronates in good to high yields with retention of the configuration using modified reaction conditions. The results of the mechanistic studies suggest that this boryl substitution proceeds via a carbanion-mediated mechanism.

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منابع مشابه

Boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with silylborane and an alkoxy base: expanded scope and mechanistic studies.

A transition-metal-free method has been developed for the boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with a silylborane in the presence of an alkali-metal alkoxide. The base-mediated boryl substitution of organohalides with a silylborane was recently reported to provide the corresponding borylated products in good to high yields, and exhibit good functional grou...

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A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide† †Electronic supplementary information (ESI) available: Experimental procedures, characterization data, and NMR spectra for compounds. See DOI: 10.1039/c6sc04371b Click here for additional data file.

We describe here a tandem catalytic route to prepare imidazoles in a single operation from aryl iodides, imines and CO. The reaction involves a catalytic carbonylation of aryl halides with imines to form 1,3dipoles, which undergo spontaneous 1,3-dipolar cycloaddition. Overall, this offers an alternative to coupling reactions to construct the (hetero)aryl-imidazole motif, where variation of the ...

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عنوان ژورنال:

دوره 6  شماره 

صفحات  -

تاریخ انتشار 2015