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Zirconium and hafnium catalyzed C-C single bond hydroboration.

ABSTRACT: Selective cleavage and subsequent functionalization of C-C single bonds present a fundamental challenge in synthetic organic chemistry. Traditionally, the activation of C-C single bonds has been achieved using stoichiometric transition-metal complexes. Recently, examples of catalytic processes were developed in which use is made of precious metals. However, the use of inexpensive and Earth-abundant group IV metals for catalytic C-C single-bond cleavage is largely underdeveloped. Herein, the zirconium-catalyzed C-C single-bond cleavage and subsequent hydroboration reactions is realized using Cp₂ZrCl₂ as a catalytic system. A series of structures of various γ-boronated amines are readily obtained, which are otherwise difficult to obtain. Mechanistic studies disclose the formation of a N-Zr^IV species, and then a β-carbon elimination route is responsible for C-C single bond activation. Besides zirconium, hafnium exhibits a similar performance for this transformation.

SUBMITTER: Li S

PROVIDER: S-EPMC10902336 | biostudies-literature | 2024 Feb

REPOSITORIES: biostudies-literature

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Zirconium and hafnium catalyzed C-C single bond hydroboration.

Li Sida S Jiao Haijun H Shu Xing-Zhong XZ Wu Lipeng L

Nature communications 20240228 1

Selective cleavage and subsequent functionalization of C-C single bonds present a fundamental challenge in synthetic organic chemistry. Traditionally, the activation of C-C single bonds has been achieved using stoichiometric transition-metal complexes. Recently, examples of catalytic processes were developed in which use is made of precious metals. However, the use of inexpensive and Earth-abundant group IV metals for catalytic C-C single-bond cleavage is largely underdeveloped. Herein, the zirc ...[more]

PMID: 38418499

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