Zirconium and hafnium catalyzed C–C single bond hydroboration

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...

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Bibliographic Details
Published inNature communications Vol. 15; no. 1; p. 1846
Main Authors Li, Sida, Jiao, Haijun, Shu, Xing-Zhong, Wu, Lipeng
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 28.02.2024
Nature Publishing Group
Nature Portfolio
Subjects
140/131
140/58
639/638/403/933
639/638/549/884
639/638/77/888
Amines
Chemical bonds
Cleavage
Coordination compounds
Hafnium
Heavy metals
Humanities and Social Sciences
Hydroboration
Metal complexes
Metals
multidisciplinary
Organic chemistry
Science
Science (multidisciplinary)
Transition metal compounds
Zirconium
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Summary: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 Cp 2 ZrCl 2 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. Selective cleavage and subsequent functionalization of C−C single bonds present a fundamental challenge, and the use of inexpensive and Earth-abundant group IV metals for catalytic C−C single-bond cleavage is largely underdeveloped. Here, the authors report zirconium-catalyzed C−C single-bond cleavage and subsequent hydroboration reactions.
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ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-024-45697-y