无金属助剂碘促进酰胺-炔的重组和立体选择性1,2-二碘化。

IF 3.3 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal Pub Date : 2024-11-29 DOI:10.1002/asia.202401531

Mohana Reddy Mutra, T. L. Chandana, Yun-Jou Wang, Jeh-Jeng Wang

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引用次数: 0

摘要

我们报道了一个无金属添加剂碘促进的一步结构重组，并同时对迁移的炔进行了立体选择性的1,2-二碘化，形成立体特异性的四取代烯基二碘系缚吲哚（e-异构体）。分子碘具有成本效益、用户友好、毒性小、可买到且易于处理的特点。该反应的主要特点包括无金属和添加剂的环境、选择性、结构重组、温和的反应条件、简单的加工和克级合成。这种转化通过N- csp键裂解产生多个键[氮(N)-碳(C)sp2, Csp2-Csp2, 2csp2 -碘(I)]。

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Metal Additive–Free Iodine–Promoted Reorganization of Ynamide-Ynes and Stereoselective 1,2-Diiodination

We report a metal additive–free iodine-promoted one-step structural reorganization of ynamide-ynes and simultaneous stereoselective 1,2-diiodination of the migrated alkyne to form stereospecific tetrasubstituted alkenyl diiodo-tethered indoles (E-isomer). Molecular iodine is cost effective, user friendly, less toxic, commercially available, and easy to handle. The key features of the reaction include metal–and additive–free environment, selectivity, structural reorganization, mild reaction conditions, simple workup, and gram-scale synthesis. This transformation generates multiple bonds [nitrogen (N)-carbon (C)sp2, Csp2−Csp2, 2 Csp2-iodine (I)] via N−Csp bond cleavage in ynamide-ynes.

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来源期刊

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).