2018
DOI: 10.1246/cl.180385
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Copper-catalyzed Borylation of Bromoaryl Triflates with Diborons: Chemoselective Replacement of an Ar–Br Bond

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Cited by 13 publications
(7 citation statements)
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“…Although various R−B(dan) (R=alkyl, alkenyl, aryl and allyl) are directly accessible by the substitution, a representative problem awaiting solution is low α/γ‐selectivity in the allylic borylation of allylic halides (Scheme ), which should result from a radical pathway operative therein. One‐electron reduction of a carbon−halogen bond sets off the radical pathway, and therefore we envisaged that use of a one‐electron reduction‐resistant leaving group instead of halogen should be promising for regiocontrol. We report herein on the copper‐catalyzed γ‐selective B(dan)‐installing allylic borylation of allylic phosphates, which proceeds not through the radical pathway.…”
Section: Methodsmentioning
confidence: 82%
“…Although various R−B(dan) (R=alkyl, alkenyl, aryl and allyl) are directly accessible by the substitution, a representative problem awaiting solution is low α/γ‐selectivity in the allylic borylation of allylic halides (Scheme ), which should result from a radical pathway operative therein. One‐electron reduction of a carbon−halogen bond sets off the radical pathway, and therefore we envisaged that use of a one‐electron reduction‐resistant leaving group instead of halogen should be promising for regiocontrol. We report herein on the copper‐catalyzed γ‐selective B(dan)‐installing allylic borylation of allylic phosphates, which proceeds not through the radical pathway.…”
Section: Methodsmentioning
confidence: 82%
“…A number of methods have been established for the synthesis of arylboronates from aryl halides employing catalytic copper/NHC, 9 copper/phosphine, 10 and other copper-based systems. 11 In addition, various copper-catalysed reactions converting alkyl halides to alkylboronates have been reported.…”
Section: Introductionmentioning
confidence: 99%
“…Yoshida et al. reported the copper‐catalyzed borylation of bromoaryl triflates with Ar−Br chemoselectivity (two examples of B 2 Pin 2 ) [6a] . Recently, Noonan et al.…”
Section: Methodsmentioning
confidence: 99%