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Gold-Catalyzed 1,2-Dicarbofunctionalization of Alkynes

25 May 2023, Version 1
Working Paper
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

Abstract

Herein, we report the first gold-catalyzed 1,2-dicarbofunctionalization of alkynes using organohalides as non-prefunctionalized coupling partners. The mechanism of the reaction involves an oxidative addition/π-activation mechanism, in contrast to the migratory insertion/cis-trans isomerization pathway that is predominantly observed with other transition metals, in order to afford products with anti-selective installation of the incoming functionalities. Mechanistic insights include several control experiments, NMR studies, HR-MSMS analyses, and DFT calculations that strongly support the proposed mechanism.

Keywords

Alkynes
Gold
Dicarbofunctionalization
Redox Catalysis
DFT Studies

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Now Published

Gold‐Catalyzed 1,2‐Dicarbofunctionalization of Alkynes with Organohalides** [opens in a new tab]
Shashank P. Sancheti, Yukta Singh, Manoj V. Mane, Nitin T. Patil journal article
Angewandte Chemie International Edition , Volume 62, Issue 42
Online publication date: Sep 07, 2023

Version History

May 25, 2023 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2023-wd2l2
D O I: 10.26434/chemrxiv-2023-wd2l2 [opens in a new tab]

Funding

SERB, New Delhi
CRG/2022/000195 and SCP/2022/000063

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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