![Author ORCID: We display the ORCID iD icon alongside authors names on our website to acknowledge that the ORCiD has been authenticated when entered by the user. To view the users ORCiD record click the icon. [opens in a new tab]](https://chemrxiv.org/engage/assets/public/chemrxiv/images/logos/orcid.png)
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.
Supplementary materials
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
Actions
