Gold-Catalyzed Oxidative Coupling of Alkynes toward the Synthesis of Cyclic Conjugated Diynes

Authors

Xiaohan Ye, University of South FloridaFollow
Haihui Peng, University of South Florida
Chiyu Wei, University of South FloridaFollow
Teng Yuan, University of South FloridaFollow
Lukasz Wojtas, University of South FloridaFollow
Xiaodong Shi, University of South FloridaFollow

Document Type

Article

Publication Date

8-2018

Keywords

gold catalysis, cyclic conjugated diynes, macrocyclization, oxidative coupling

Digital Object Identifier (DOI)

https://doi.org/10.1016/j.chempr.2018.07.004

Abstract

Gold-catalyzed oxidative coupling of alkynes was developed as an efficient approach for the synthesis of challenging cyclic conjugated diynes (CCD). Compared with the classic copper-promoted oxidative coupling reaction of alkynes, this gold-catalyzed process exhibited a faster reaction rate due to rapid reductive elimination from the Au(III) intermediate. This unique reactivity thus allowed a challenging diyne macrocyclization to take place with high efficiency. Condition screening revealed an [(n-Bu)₄N]⁺[Cl-Au-Cl]⁻ salt as the optimal pre-catalyst. Macrocycles with ring size between 13 and 28 atoms were prepared in moderate to good yields, which highlighted the broad substrate scope of this new strategy. Furthermore, the synthetic utilities of the CCDs for copper-free click chemistry have been demonstrated, showcasing the potential application of this strategy in biological systems.

Was this content written or created while at USF?

Yes

Citation / Publisher Attribution

Chem, v. 4, issue 8, p. 1983-1993

Scholar Commons Citation

Ye, Xiaohan; Peng, Haihui; Wei, Chiyu; Yuan, Teng; Wojtas, Lukasz; and Shi, Xiaodong, "Gold-Catalyzed Oxidative Coupling of Alkynes toward the Synthesis of Cyclic Conjugated Diynes" (2018). Chemistry Faculty Publications. 64.
https://digitalcommons.usf.edu/chm_facpub/64