C—H Activation of Unbiased C(sp3)—H Bonds

13 December 2022, Version 4
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The selective functionalization of non-activated C(sp3)—H bonds is a major challenge in chemistry. Here, we have developed an [Au]-catalyzed C(sp3)-H activation of common 1 bromoalkynes into a library of diverse 3D-scaffolds. The reaction was shown to proceed via an unknown before mechanism: a concerted [1,5]-H shift / C—C bond formation involving a gold-stabilized vinylcation-like transition state. The most salient feature of this methodology is the ability to functionalize in a predictable way non-activated C(sp3)—H bonds without any sort of electronic, geometric, or conformational bias.

Keywords

gold-catalysis
bromoalkynes
C-H activation
molecular diversity

Supplementary materials

Title
Description
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Title
Experimental procedures, spectroscopic data and computational details
Description
Experimental procedures for the synthesis of starting materials and final products. Full caracterization of staring materials and final products. KIE determination experiments. 13C isotope labelling experiments. X-ray structures. Computational study
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