Convergent Synthesis of the Precursors to Thiophene-Based Quinoids

Renzhen Fan; Tian Du; Yiyang Xu; Cheng Wang; Tingting Xu; Yi Han; Chunyan Chi; Yunfeng Deng; Yanhou Geng

doi:10.1021/acs.orglett.3c00479

Convergent Synthesis of the Precursors to Thiophene-Based Quinoids

Org Lett. 2023 Apr 21;25(15):2565-2570. doi: 10.1021/acs.orglett.3c00479. Epub 2023 Apr 12.

Authors

Renzhen Fan¹, Tian Du², Yiyang Xu², Cheng Wang², Tingting Xu³, Yi Han³, Chunyan Chi³, Yunfeng Deng^{1

2}, Yanhou Geng^{1

2}

Affiliations

¹ Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou 350207, China.
² School of Materials Science and Engineering and Tianjin Key Laboratory of Molecular Optoelectronic Science, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China.
³ Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.

PMID: 37043302
DOI: 10.1021/acs.orglett.3c00479

Abstract

A convergent (outside-to-center) route was adopted to synthesize the precursors of quinoidal compounds in high yields of 85-93%. With subsequent rearrangement/dehydroxylation and oxidation, a series of thiophene-based quinoids with indandione or oxindole terminal groups were successfully synthesized. This strategy shows good compatibility with versatile central and terminal units, leading to quinoidal compounds with tunable properties.