A modular approach to highly functionalized 3-sulfonylfurans via conjugate addition of 3-cyclopropylideneprop-2-en-1-ones with sodium sulfinates and sequential 5-endo-trig iodocyclization

Maozhong Miao; Huaping Xu; Yi Luo; Mengchao Jin; Zhengkai Chen; Jianfeng Xu; Hongjun Ren

doi:10.1039/C7QO00362E

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A modular approach to highly functionalized 3-sulfonylfurans via conjugate addition of 3-cyclopropylideneprop-2-en-1-ones with sodium sulfinates and sequential 5-endo-trig iodocyclization†

Maozhong Miao,

*^a Huaping Xu,^a Yi Luo,^a Mengchao Jin,^a Zhengkai Chen,

^a Jianfeng Xu

^a and Hongjun Ren*^a

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* Corresponding authors

^a Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, China
E-mail: mmzok@zstu.edu.cn, renhj@zstu.edu.cn

Abstract

A highly efficient conjugate addition and 5-endo-trig cyclization reaction of 3-cyclopropylideneprop-2-en-1-ones with sodium sulfinates in the presence of iodine is described. A wide variety of densely functionalized 3-sulfonylfurans are furnished by single-step and one-pot methods, respectively. The results of such postcyclization modifications are also presented.

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DOI: https://doi.org/10.1039/C7QO00362E
Article type: Research Article
Submitted: 08 May 2017
Accepted: 13 Jun 2017
First published: 14 Jun 2017

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Org. Chem. Front., 2017,4, 1824-1828

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A modular approach to highly functionalized 3-sulfonylfurans via conjugate addition of 3-cyclopropylideneprop-2-en-1-ones with sodium sulfinates and sequential 5-endo-trig iodocyclization

M. Miao, H. Xu, Y. Luo, M. Jin, Z. Chen, J. Xu and H. Ren, Org. Chem. Front., 2017, 4, 1824 DOI: 10.1039/C7QO00362E

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Organic Chemistry Frontiers

A modular approach to highly functionalized 3-sulfonylfurans via conjugate addition of 3-cyclopropylideneprop-2-en-1-ones with sodium sulfinates and sequential 5-endo-trig iodocyclization†

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A modular approach to highly functionalized 3-sulfonylfurans via conjugate addition of 3-cyclopropylideneprop-2-en-1-ones with sodium sulfinates and sequential 5-endo-trig iodocyclization

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