Reactivity of NHC/diphosphene-coordinated Au(I)-hydride

Debabrata Dhara; David Scheschkewitz; Vadapalli Chandrasekhar; Cem B. Yildiz; Anukul Jana

doi:10.1039/D0CC05461E

Reactivity of NHC/diphosphene-coordinated Au(i)-hydride†

Debabrata Dhara,

^a David Scheschkewitz,

*^b Vadapalli Chandrasekhar,

*^ac Cem B. Yildiz

*^d and Anukul Jana

*^a

Author affiliations

* Corresponding authors

^a Tata Institute of Fundamental Research Hyderabad, Gopanpally, Hyderabad-500046, Telangana, India
E-mail: ajana@tifrh.res.in

^b Krupp-Chair of General and Inorganic Chemistry, Saarland University, 66123 Saarbrücken, Germany
E-mail: scheschkewitz@mx.uni-saarland.de

^c Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur-208016, India
E-mail: vc@iitk.ac.in

^d Department of Medicinal and Aromatic Plants, University of Aksaray, Aksaray, Turkey
E-mail: cemburakyildiz@aksaray.edu.tr

Abstract

We report the reactivity of isolable Au(I)-hydride stabilized by an NHC-coordinated diphosphene towards substrates containing C–C and N–N multiple bonds (NHC = N-heterocyclcic carbene). Reactions with dimethyl acetylenedicarboxylate and azobenzene lead to a trans-addition of the Au(I)-H across the C–C triple bond and the N–N double bond, respectively. In contrast, the reaction with ethyl diazoacetate affords a gold(I)-hydrazonide as the 1,1-addition product to the terminal nitrogen atom. With phenyl acetylene, the corresponding Au(I)-alkynyl complex is obtained under the elimination of dihydrogen. Strikingly, diphosphene-containing Au(I)-hydride is more reactive – affording different products in some cases – than a related NHC-stabilized Au(I)-hydride without the mediating diphosphene moiety.

Supplementary files

Article information

DOI: https://doi.org/10.1039/D0CC05461E
Article type: Communication
Submitted: 11 Aug 2020
Accepted: 08 Dec 2020
First published: 14 Dec 2020

Download Citation

Chem. Commun., 2021,57, 809-812

Permissions

Request permissions

Reactivity of NHC/diphosphene-coordinated Au(I)-hydride

D. Dhara, D. Scheschkewitz, V. Chandrasekhar, C. B. Yildiz and A. Jana, Chem. Commun., 2021, 57, 809 DOI: 10.1039/D0CC05461E

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.

Chemical Communications

Reactivity of NHC/diphosphene-coordinated Au(i)-hydride†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Reactivity of NHC/diphosphene-coordinated Au(I)-hydride

Social activity

Search articles by author

Spotlight

Advertisements