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Rh(ii)-catalyzed branch-selective C-H alkylation of aryl sulfonamides with vinylsilanes.

ABSTRACT: Rhodium(ii)-catalyzed unusual branch-selective ortho-C-H alkylation of aryl sulfonamides with vinylsilanes was achieved using an 8-aminoquinoline directing group. Notably, the para-substituted aryl sulfonamides gave mono-(branched)alkylated products exclusively without the formation of any double C-H alkylated byproducts. The results of deuterium labeling experiments suggest that both hydrometalation and carbometalation pathways are involved in this conversion.

SUBMITTER: Rej S

PROVIDER: S-EPMC7069504 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Rh(ii)-catalyzed branch-selective C-H alkylation of aryl sulfonamides with vinylsilanes.

Rej Supriya S Chatani Naoto N

Chemical science 20191111 2

Rhodium(ii)-catalyzed unusual branch-selective <i>ortho</i>-C-H alkylation of aryl sulfonamides with vinylsilanes was achieved using an 8-aminoquinoline directing group. Notably, the <i>para</i>-substituted aryl sulfonamides gave mono-(branched)alkylated products exclusively without the formation of any double C-H alkylated byproducts. The results of deuterium labeling experiments suggest that both hydrometalation and carbometalation pathways are involved in this conversion. ...[more]

PMID: 32206270

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