Rhodium(II)-catalyzed intermolecular [3 + 2] annulation of N-vinyl indoles with N-tosyl-1,2,3-triazoles via an aza-vinyl Rh carbene,Organic Chemistry Frontiers

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Rhodium(II)-catalyzed intermolecular [3 + 2] annulation of N-vinyl indoles with N-tosyl-1,2,3-triazoles via an aza-vinyl Rh carbene
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2017-09-12 00:00:00 , DOI: 10.1039/c7qo00703e
Bo Jiang _{1,

2,

3,

4,

5} , Min Shi _{1,

2,

3,

4,

5}

Affiliation

The rhodium(II)-catalyzed annulations of N-vinyl indole derivatives and N-tosyl-1,2,3-triazoles have been developed in this paper, providing a convenient, efficient and straightforward access to synthesize indoles containing a N-dihydropyrrole in moderate to good yields. Furthermore, the reaction of N-vinyl indoles with 2.5 equiv. of N-tosyl-1,2,3-triazoles gave C3-functionalized indoles containing a N-dihydropyrrole in moderate yields after reduction with NaBH₃CN in a one-pot manner. This finding gives a new synthetic protocol for the preparation of indoles containing a N-dihydropyrrole under mild conditions.

中文翻译：

铑（II）通过氮杂乙烯基Rh卡宾与N-甲苯磺酰基-1,2,3-三唑的N-乙烯基吲哚分子间[3 + 2]环化反应

本文开发了铑（II）催化的N-乙烯基吲哚衍生物和N-甲苯磺酰基-1,2,3-三唑的环化反应，为合成含N-二氢吡咯的吲哚提供了方便，有效和直接的途径。中等至良好的产量。此外，N-乙烯基吲哚与2.5当量的反应。在一锅法中用NaBH ₃ CN还原后，N-甲苯磺酰基-1,2,3-三唑的合成得到中等收率的含有N-二氢吡咯的C3-官能化的吲哚。这一发现为制备含N的吲哚提供了一种新的合成方案。-二氢吡咯在温和的条件下。

更新日期：2017-09-20

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