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从炔基碘翁盐到芳基[1,2-a]咪唑并吡啶的形成中前所未有的区域化学控制:机理见解。

Unprecedented regiochemical control in the formation of aryl[1,2-a]imidazopyridines from alkynyliodonium salts: mechanistic insights.

机构信息

School of Chemistry, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK.

出版信息

Org Biomol Chem. 2013 Sep 21;11(35):5877-84. doi: 10.1039/c3ob41112e.

DOI:10.1039/c3ob41112e
PMID:23903567
Abstract

Aryl(alkynyl)iodonium salts have been demonstrated to be valuable precursors to a diverse range of heteroaromatic ring systems including aryl[1,2-a]imidazopyridines. Successful application, using the recently described aryl(alkynyl)iodonium trifluoroacetate salts, is described, highlighting for the first time that the regioselectivity of this process is both counter-ion and concentration dependent. Studies with a carbon-13 labelled substrate established that the reactions of alkynyliodonium salts are highly complex and that multiple mechanistic processes appear to be underway simultaneously.

摘要

芳基(炔基)碘𬭩盐已被证明是制备各种杂芳环体系的有价值的前体,包括芳基[1,2-a]咪唑并吡啶。成功地应用了最近描述的芳基(炔基)碘𬭩三氟乙酸盐,首次强调了该过程的区域选择性既依赖于反离子又依赖于浓度。使用 13C 标记的底物进行的研究表明,炔基碘𬭩盐的反应非常复杂,似乎同时进行多种机理过程。

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