Efficient preparation of unsymmetrical disulfides by nickel-catalyzed reductive coupling strategy

Fei Wang, Ying Chen, Weidong Rao, Lutz Ackermann () and Shun-Yi Wang ()
Additional contact information
Fei Wang: Collaborative Innovation Center of Suzhou Nano Science and Technology Soochow University
Ying Chen: Collaborative Innovation Center of Suzhou Nano Science and Technology Soochow University
Weidong Rao: Nanjing Forestry University
Lutz Ackermann: Institut für Organische und Biomolekulare Chemie Georg-August-Universität Göttingen Tammannstraße 2
Shun-Yi Wang: Collaborative Innovation Center of Suzhou Nano Science and Technology Soochow University

Nature Communications, 2022, vol. 13, issue 1, 1-10

Abstract: Abstract Disulfides are widely found in natural products and find a wide range of applications in life sciences, materials chemistry and other fields. The preparation of disulfides mainly rely on oxidative couplings of two sulfur containing compounds. This strategy has many side reactions and other shortcomings. Herein, we describe the reductive nickel-catalyzed cross-electrophile coupling of unactivated alkyl bromides with symmetrical alkyl- and aryltetrasulfides to form alkyl-alkyl and aryl-alkyl unsymmetrical disulfides. This approach for disulfide synthesis is practical, relies on easily available, unfunctionalized substrates, and is scalable. We investigated the mechanism of this transformation and found that the tetrasulfide compound does not selectively break the central S–S bond, but regio-selectively generates trisulfide intermediates.

Date: 2022
References: View references in EconPapers View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-022-30256-0 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30256-0

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-022-30256-0

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().