Direct oxidative installation of nitrooxy group at benzylic positions and its transformation into various functionalities

被引：41

作者：

Kamijo, Shin ^{[1
]}

Amaoka, Yuuki ^{[1
]}

Inoue, Masayuki ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 36期

关键词：

Catalysis; Nitrooxylation; Benzylic position; N-Hydroxyphthalimide; Cerium(IV) ammonium nitrate; CERIUM(IV) AMMONIUM-NITRATE; C-H OXIDATION; N-HYDROXYPHTHALIMIDE; ALKANES; EFFICIENT; CATALYST; OXYGEN; METHYLBENZENES; ACYLOXYLATION; HYDROCARBONS;

D O I：

10.1016/j.tetlet.2011.06.118

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

C-H Nitrooxylation at benzylic positions has been achieved by employing the N-hydroxyphthalimide (NHPI) catalyst/cerium(IV) ammonium nitrate (CAN) reagent system. The nitrooxy groups were demonstrated to function as tentative hydroxy protecting groups, as well as excellent leaving groups for N- and C-substitution reactions. Hence, the present method offers a unique way to synthesize diverse O-. N-, or C-functionalized benzylic compounds from simple alkyl aromatics. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：4654 / 4657

页数：4

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