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Expanding the functional group tolerance of cross-coupling in 1,2-dihydro-1,2-azaborines: installation of alkyl, alkenyl, aryl, and heteroaryl substituents while maintaining a B-H bond.

ABSTRACT: Palladium-catalyzed Negishi cross-coupling of 3-bromo-1-(tert-butyldimethylsilyl)-1,2-dihydro-1,2-azaborine while maintaining the B-H functionality has been demonstrated. 17 examples, including dialkylzinc, alkyl-, alkenyl-, aryl-, as well as nitrogen-, sulfur-, and oxygen-containing heteroaryl-zinc halide reagents have been coupled to generate new C(3) substituted 1,2-azaborines in moderate to excellent yields.

SUBMITTER: Brown AN

PROVIDER: S-EPMC6752210 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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Expanding the functional group tolerance of cross-coupling in 1,2-dihydro-1,2-azaborines: installation of alkyl, alkenyl, aryl, and heteroaryl substituents while maintaining a B-H bond.

Brown Alec N AN Li Bo B Liu Shih-Yuan SY

Tetrahedron 20181222 5

Palladium-catalyzed Negishi cross-coupling of 3-bromo-1-(tert-butyldimethylsilyl)-1,2-dihydro-1,2-azaborine while maintaining the B-H functionality has been demonstrated. 17 examples, including dialkylzinc, alkyl-, alkenyl-, aryl-, as well as nitrogen-, sulfur-, and oxygen-containing heteroaryl-zinc halide reagents have been coupled to generate new C(3) substituted 1,2-azaborines in moderate to excellent yields. ...[more]

PMID: 31537948

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