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The serendipitous effect of KF in Ritter reaction: Photo-induced amino-alkylation of alkenes.

ABSTRACT: Ritter reaction has been recognized as an elegant strategy to construct the C-N bond. Its key feature is forming the carbocation for nucleophilic attack by nitriles. Herein, we report a complementary visible-light-induced three-component Ritter reaction of alkenes, nitriles, and α-bromo nitriles/esters, thereby providing mild and rapid access to various γ-amino nitriles/acids. Mechanistic studies indicated that traceless fluoride relay, transforming KF into imidoyl fluoride intermediate, is critical for the efficient reaction switch from atom transfer radical addition (ATRA) to the Ritter reaction. This approach to amino-alkylation of alkenes is chemoselective and operationally simple.

SUBMITTER: Guan YQ

PROVIDER: S-EPMC8383004 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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The serendipitous effect of KF in Ritter reaction: Photo-induced amino-alkylation of alkenes.

Guan Yu-Qing YQ Min Xiang-Ting XT He Gu-Cheng GC Ji Ding-Wei DW Guo Shi-Yu SY Hu Yan-Cheng YC Chen Qing-An QA

iScience 20210811 9

Ritter reaction has been recognized as an elegant strategy to construct the C-N bond. Its key feature is forming the carbocation for nucleophilic attack by nitriles. Herein, we report a complementary visible-light-induced three-component Ritter reaction of alkenes, nitriles, and α-bromo nitriles/esters, thereby providing mild and rapid access to various γ-amino nitriles/acids. Mechanistic studies indicated that traceless fluoride relay, transforming KF into imidoyl fluoride interme ...[more]

PMID: 34466792

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