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. 2016 Jul 13;138(27):8408-11.
doi: 10.1021/jacs.6b05436. Epub 2016 Jul 1.

Additive- and Metal-Free, Predictably 1,2- and 1,3-Regioselective, Photoinduced Dual C-H/C-X Borylation of Haloarenes

Adelphe M Mfuh  1 , Vu T Nguyen  1 , Bhuwan Chhetri  1 , Jessica E Burch  1 , John D Doyle  1 , Vladimir N Nesterov  2 , Hadi D Arman  1 , Oleg V Larionov  1
Affiliations

Additive- and Metal-Free, Predictably 1,2- and 1,3-Regioselective, Photoinduced Dual C-H/C-X Borylation of Haloarenes

Adelphe M Mfuh et al. J Am Chem Soc. .

Abstract

We report herein a simple, additive- and metal-free, photoinduced, dual C-H/C-X borylation of chloro-, bromo-, and iodoarenes. The reaction produces 1,2- and 1,3-diborylarenes on gram scales under batch and continuous flow conditions. The regioselectivity of the dual C-H/C-X borylation is determined by the solvent and the substituents in the parent haloarenes.

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Figures

Scheme 1
Scheme 1
Photoinduced 1,2- and 1,3-Selective Dual C–H/C–X Borylation Reaction of Haloarenes
Scheme 2
Scheme 2
Plausible Reaction Pathways for the Photoinduced Dual C–H/C–X-Borylation
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