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含氟亚胺酰氯与PhPNNC的可控区域选择性[3+2]环化反应:含氟三唑的发散合成

Controllable Regioselective [3+2] Cyclizations of -CF Imidoyl Chlorides and PhPNNC: Divergent Synthesis of -CF Triazoles.

作者信息

Gao Yan Fang, Zhang Ru Zhong, Xu Cong, Wang Mang

机构信息

Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, College of Chemistry, Northeast Normal University, 5268 Renmin Street, Changchun 130024, China.

出版信息

Org Lett. 2024 Jun 21;26(24):5087-5091. doi: 10.1021/acs.orglett.4c01275. Epub 2024 Jun 12.

Abstract

Presented herein are two distinct regiodivergent [3+2] cyclization reactions between -CF imidoyl chlorides and -isocyaniminotriphenylphosphorane (NIITP) that include flexible modulation of the electronic properties of NIITP. The regioselectivity of reactions was different in the absence and presence of the Mo catalyst. The approach provides alternative efficient and scalable routes for -CF triazole synthesis, demonstrating a broad substrate scope, excellent functional group tolerance, and practical advantages.

摘要

本文介绍了两种不同的区域发散性[3+2]环化反应,反应发生在-CF亚胺酰氯和-异氰基亚胺基三苯基膦(NIITP)之间,其中包括对NIITP电子性质的灵活调节。在不存在和存在钼催化剂的情况下,反应的区域选择性不同。该方法为-CF三唑的合成提供了替代的高效且可扩展的路线,展示了广泛的底物范围、出色的官能团耐受性和实际优势。

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