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

TETRAHEDRON

卷:75

Article

Brown, Alec N.^1,2  Li, Bo¹  Liu, Shih-Yuan¹ 

[1] Boston Coll, Dept Chem, Chestnut Hill, MA 02467 USA

[2] St Ambrose Univ, Chem Dept, Davenport, IA 52803 USA

关键词: Boron heterocycles;    Azaborines;    Cross coupling;   

DOI  :  10.1016/j.tet.2018.12.039

来源: Elsevier

【 摘 要 】

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. (C) 2018 Elsevier Ltd. All rights reserved.

【 授权许可】

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