Photochemically induced radical alkenylation of C(sp3)-H bonds

被引：103

作者：

Amaoka, Yuuki ^{[1
]}

Nagatomo, Masanori ^{[1
]}

Watanabe, Mizuki ^{[2
]}

Tao, Keisuke ^{[2
]}

Kamijo, Shin ^{[2
]}

Inoue, Masayuki ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

[2] Yamaguchi Univ, Grad Sch Sci & Engn, Yamaguchi 7538512, Japan

来源：

CHEMICAL SCIENCE | 2014年 / 5卷 / 11期

关键词：

C-H BONDS; TRISUBSTITUTED VINYL TRIFLONES; COUPLING REACTIONS; ORGANIC-SYNTHESIS; MOLECULAR-OXYGEN; NATURAL-PRODUCTS; SYNTHETIC TOOLS; METAL-FREE; SULFONES; FUNCTIONALIZATION;

D O I：

10.1039/c4sc01631a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The direct alkenylation of C(sp(3))-H bonds was achieved by employing benzophenone and 1,2-bis(phenylsulfonyl) ethylene under photo-irradiation conditions. This simple metal-free reaction enables the substitution of heteroatom-substituted methine, methylene and aliphatic C(sp(3))-H bonds by (E)-sulfonylalkene units in a highly chemoselective manner. The derived sulfonylalkenes were further converted in a single step to the prenyl derivatives via a second photo-induced radical substitution and to the pyrrole derivatives via cyclization and aromatization steps. The present protocol thus serves as an efficient method for the direct extension of carbon skeletons for the synthesis of structurally complex natural products and pharmaceuticals.

引用

页码：4339 / 4345

页数：7

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