Remote C(sp3)—H insertion into non-activated bonds: rapid construction of an added-value molecular diverse library

25 April 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The synthesis of added-value compounds from raw feedstock materials represents one of the major challenges in synthetic organic chemistry. By using a well-defined intramolecular C—H insertion reaction, it is possible to transform a number of raw feedstock compounds into a library of molecularly complex and diverse compounds. In addition, these compounds display a C—Br bond amenable for further functionalization. A preliminary mechanistic study supports the participation of an elusive gold (I) vinylidene complex as key intermediate of the reaction. The most salient feature of this methodology is the ability to functionalize in a predictable way non-activated C—H bonds without any sort of electronic, geometric or conformational bias.

Keywords

gold-catalysis
bromoalkynes
C-H activation
molecular diversity

Supplementary materials

Title
Description
Actions
Title
Experimental procedures and spectroscopic data
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
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.