Organic Chemistry Portal

Abstracts

Search:

Design, Generation, and Synthetic Application of Borylzincate: Borylation of Aryl Halides and Borylzincation of Benzynes/Terminal Alkyne

Yuki Nagashima, Ryo Takita*, Kengo Yoshida, Keiichi Hirano and Masanobu Uchiyama*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Email: takitamol.f.u-tokyo.ac.jp, uchiyamamol.f.u-tokyo.ac.jp

Y. Nagashima, R. Takita, K. Yoshida, K. Hirano, M. Uchiyama, J. Am. Chem. Soc., 2013, 135, 18730-18733.

DOI: 10.1021/ja409748m (free Supporting Information)


see article for more reactions

Abstract

Borylzincate can be generated in situ from dialkylzinc, diboron, and metal alkoxide. Model DFT calculations show that although the formation of borylzincate is kinetically favorable, it is thermodynamically unfavorable. A successive reaction sequence, that provides a compensating energy gain, therefore enables Zn-catalyzed borylation of aryl halides and borylzincation of benzynes and terminal alkyne from diborons without the need for any cocatalyst.

see article for more examples



Key Words

borylation


ID: J48-Y2013