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Chromium-catalyzed cyclopropanation of alkenes with bromoform in the presence of 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-dihydropyrazine.

ABSTRACT: Chromium-catalyzed cyclopropanation of alkenes with bromoform was achieved to produce the corresponding bromocyclopropanes. In this catalytic cyclopropanation, an organosilicon reductant, 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-dihydropyrazine (1a), was indispensable for reducing CrCl₃(thf)₃ to CrCl₂(thf)₃, as well as for in situ generation of (bromomethylidene)chromium(iii) species from (dibromomethyl)chromium(iii) species. The (bromomethylidene)chromium(iii) species are proposed to react spontaneously with alkenes to give the corresponding bromocyclopropanes. This catalytic cyclopropanation was applied to various olefinic substrates, such as allyl ethers, allyl esters, terminal alkenes, and cyclic alkenes.

SUBMITTER: Ikeda H

PROVIDER: S-EPMC8152687 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Chromium-catalyzed cyclopropanation of alkenes with bromoform in the presence of 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-dihydropyrazine.

Ikeda Hideaki H Nishi Kohei K Tsurugi Hayato H Mashima Kazushi K

Chemical science 20200311 14

Chromium-catalyzed cyclopropanation of alkenes with bromoform was achieved to produce the corresponding bromocyclopropanes. In this catalytic cyclopropanation, an organosilicon reductant, 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-dihydropyrazine (1a), was indispensable for reducing CrCl3(thf)3 to CrCl2(thf)3, as well as for in situ generation of (bromomethylidene)chromium(iii) species from (dibromomethyl)chromium(iii) species. The ( ...[more]

PMID: 34094048

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