Dearomative ring expansion of thiophenes by bicyclobutane insertion

IF 47.3 1区综合性期刊 Q1 MULTIDISCIPLINARY SCIENCES

Science Pub Date : 2023-07-06 DOI:10.1126/science.adh9737

Huamin Wang, Huiling Shao, Ankita Das, Subhabrata Dutta, Hok Tsun Chan, Constantin Daniliuc, K. N. Houk, Frank Glorius

引用次数: 4

Abstract

Skeletal ring enlargement is gaining renewed interest in synthetic chemistry and has recently focused on insertion of one or two atoms. Strategies for heterocyclic expansion through small-ring insertion remain elusive, although they would lead to the efficient formation of bicyclic products. Here, we report a photoinduced dearomative ring enlargement of thiophenes by insertion of bicyclo[1.1.0]butanes to produce eight-membered bicyclic rings under mild conditions. The synthetic value, broad functional-group compatibility, and excellent chemo- and regioselectivity were demonstrated by scope evaluation and product derivatization. Experimental and computational studies point toward a photoredox-induced radical pathway.

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通过插入双环丁烷实现噻吩的异构扩环

骨架环扩大在合成化学中再次引起人们的兴趣，最近的研究重点是插入一个或两个原子。通过小环插入进行杂环扩环的策略仍然难以捉摸，尽管这些策略可以有效地形成双环产品。在此，我们报告了在温和的条件下，通过插入双环[1.1.0]丁烷对噻吩进行光诱导脱芳扩环，从而生成八元双环。其合成价值、广泛的官能团兼容性以及出色的化学和区域选择性已通过范围评估和产物衍生得到证实。实验和计算研究指出了光氧化诱导的自由基途径。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Science 综合性期刊-综合性期刊

CiteScore

61.10

自引率

0.90%

发文量

审稿时长

2.1 months

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