Issue 18, 2022

Alkynyl transmetalation triggered by a nucleophilic attack

Abstract

We report an interesting alkynyl transmetalation process in the cyclization of π-Au, σ-M acetylides (M = Pd, Ni, Pt) bearing a N-propiolic formamidine moiety. The cyclization was triggered by nucleophilic attack and afforded 5-membered heterodinuclear M/Au vinylidene species through a 5-exo-dig mode followed by ring-opening and recyclization to give their 6-membered endo-isomers at an elevated temperature. This suggests that the regiochemistry (5-exo vs. 6-endo) observed in the cyclization is kinetically and thermodynamically controlled. The mechanism of the domino cyclization/ring-opening/recyclization reaction is analyzed by DFT calculations.

Graphical abstract: Alkynyl transmetalation triggered by a nucleophilic attack

Supplementary files

Article information

Article type
Research Article
Submitted
16 Feb 2022
Accepted
22 Jul 2022
First published
22 Jul 2022

Inorg. Chem. Front., 2022,9, 4801-4807

Alkynyl transmetalation triggered by a nucleophilic attack

J. Wang, L. Liu, L. Zhan and J. Zhang, Inorg. Chem. Front., 2022, 9, 4801 DOI: 10.1039/D2QI00357K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements