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Directed B–H functionalization of the closo-dodecaborate cluster via concerted iodination–deprotonation: reaction mechanism and origins of regioselectivity

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Abstract

Understanding the reaction mechanism and regioselectivity control is critical for the rational synthesis of functionalized boron clusters. Herein we report a computational mechanistic study on the phenyliodo diacetate-mediated B–H functionalization of the amide-substituted closo-dodecaborate cluster. A concerted iodination–deprotonation process was identified for the key B–H bond iodination, which is the mechanistic basis for the exceptional regioselectivity of ortho-B–H functionalization. This mechanistic model highlights a distinctive reaction channel for iodine(III)-promoted transformations, which paves the way for future design of directing groups in closo-dodecaborate derivatization using this strategy.

Graphical abstract: Directed B–H functionalization of the closo-dodecaborate cluster via concerted iodination–deprotonation: reaction mechanism and origins of regioselectivity

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Article information


Submitted
25 Aug 2020
Accepted
08 Oct 2020
First published
09 Oct 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Directed B–H functionalization of the closo-dodecaborate cluster via concerted iodination–deprotonation: reaction mechanism and origins of regioselectivity

T. Zhu, Y. Xing, Y. Sun, S. Duttwyler and X. Hong, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO01019G

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