Facile synthesis of fluorescent active triazapentalenes through gold-catalyzed triazole–alkyne cyclization

Rong Cai; Dawei Wang; Yunfeng Chen; Wuming Yan; Natalie R. Geise; Sripadh Sharma; Huiyuan Li; Jeffrey L. Petersen; Minyong Li; Xiaodong Shi

doi:10.1039/C4CC03175J

Facile synthesis of fluorescent active triazapentalenes through gold-catalyzed triazole–alkyne cyclization†

Rong Cai,^a Dawei Wang,^a Yunfeng Chen,^a Wuming Yan,^a Natalie R. Geise,^a Sripadh Sharma,^a Huiyuan Li,^b Jeffrey L. Petersen,^a Minyong Li*^c and Xiaodong Shi*^a

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^a C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506, USA
E-mail: Xiaodong.Shi@mail.wvu.edu
Fax: +1-304-293-4904
Tel: +1-304-293-0179

^b BioNano Research Facility, West Virginia University, Morgantown, WV 26506, USA

^c Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (MOE), School of Pharmacy, Shandong University, Jinan, Shandong, China

Abstract

Fluorescent active triazapentalene zwitterions (TAPZs) were prepared through Au(I) catalyzed triazole–alkyne 5-endo-dig cyclization. While an effective gold catalyst turnover (0.5% loading, up to 96% yield) was achieved, the stability of these new 10-π-electron bicyclic structures was also significantly improved, which warranted future applications of these fluorescent dyes.

Chemical Communications

Facile synthesis of fluorescent active triazapentalenes through gold-catalyzed triazole–alkyne cyclization†

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Facile synthesis of fluorescent active triazapentalenes through gold-catalyzed triazole–alkyne cyclization

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