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Investigations of alkynylbenziodoxole derivatives for radical alkynylations in photoredox catalysis.

ABSTRACT: The alkynylbenziodoxole derivatives are recently developed alkynylation reagents in organic synthesis, which demonstrate excellent radical alkynylation reactivity in photoredox catalysis reactions. Herein we report the synthesis of alkynylbenziodoxole derivatives with difluoro, monofluoro, monomethoxy, and dimethoxy substitution on the benziodoxole moiety, and investigated their radical alkynylation reactivity for the first time. A series of mechanistic experiments were conducted to study the radical acceptor and oxidative quencher reactivity of alkynylbenziodoxoles, in which unsubstituted alkynylbenziodoxoles played balancing roles in both processes, while electron-rich benziodoxole derivatives demonstrate synthetic advantages in some cases.

SUBMITTER: Pan Y

PROVIDER: S-EPMC6009179 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Investigations of alkynylbenziodoxole derivatives for radical alkynylations in photoredox catalysis.

Pan Yue Y Jia Kunfang K Chen Yali Y Chen Yiyun Y

Beilstein journal of organic chemistry 20180528

The alkynylbenziodoxole derivatives are recently developed alkynylation reagents in organic synthesis, which demonstrate excellent radical alkynylation reactivity in photoredox catalysis reactions. Herein we report the synthesis of alkynylbenziodoxole derivatives with difluoro, monofluoro, monomethoxy, and dimethoxy substitution on the benziodoxole moiety, and investigated their radical alkynylation reactivity for the first time. A series of mechanistic experiments were conducted to study the ra ...[more]

PMID: 29977389

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