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Cyclic Diaryl λ³-Chloranes: Reagents and Their C-C and C-O Couplings with Phenols via Aryne Intermediates.

ABSTRACT: Hypervalent chloranes are a class of rare and poorly explored reagents. Their unique electronic properties confer reactivity that is complementary to that of the common iodanes and emerging bromanes. Highly chemo- and regioselective, metal-free, and mild C-C and C-O couplings are reported here. Experimental and computational mechanistic studies elucidate the unprecedented reactivities and selectivities of these systems and the intermediacy of aryne intermediates. The synthetic potential of these transformations is further demonstrated via the post-functionalization of C-C and C-O coupling products obtained from reactions of chloranes with phenols under different conditions.

SUBMITTER: Lanzi M

PROVIDER: S-EPMC9837845 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature

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Cyclic Diaryl λ3-Chloranes: Reagents and Their C-C and C-O Couplings with Phenols via Aryne Intermediates.

Lanzi Matteo M Rogge Torben T Truong Tan Sang TS Houk K N KN Wencel-Delord Joanna J

Journal of the American Chemical Society 20221219 1

Hypervalent chloranes are a class of rare and poorly explored reagents. Their unique electronic properties confer reactivity that is complementary to that of the common iodanes and emerging bromanes. Highly chemo- and regioselective, metal-free, and mild C-C and C-O couplings are reported here. Experimental and computational mechanistic studies elucidate the unprecedented reactivities and selectivities of these systems and the intermediacy of aryne intermediates. The synthetic potential of these ...[more]

PMID: 36535642

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