Zirconium/Nickel-Mediated One-Pot Ketone Synthesis

被引：44

作者：

Ai, Yanran ^{[1
]}

Ye, Ning ^{[1
]}

Wang, Qiaoyi ^{[1
]}

Yahata, Kenzo ^{[1
]}

Kishi, Yoshito ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 36期

关键词：

ketones; nickel; radical reactions; transition-metal catalysis; zirconium; CATALYZED CONJUGATE ADDITION; METAL-PROMOTED CYCLIZATION; ALKYL-HALIDES; CONVENIENT METHOD; ARYL HALIDES; ZIRCONOCENE; COMPLEXES; DERIVATIVES; 1,3-DITHIANES; DICHLORIDE;

D O I：

10.1002/anie.201705520

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A zirconium/nickel-mediated one-pot synthesis of ketones is reported. In the presence of Zn or Mn, Cp2ZrCl2 was found to dramatically accelerate the coupling and suppress side product formation via an I -> SPy displacement at the same time. Unlike Zn/Pd- and Fe/Cu-mediated one-pot ketone syntheses, the new method is effective for nucleophiles bearing OR or equivalent functional groups at the alpha-position. A mechanism comprising a nickel catalytic cycle, a zirconium catalytic cycle, and Zr -> Ni transmetalation is proposed, and Cp2ZrCl2 and/or low-valent Zr species are suggested to play crucial dual roles.

引用

页码：10791 / 10795

页数：5

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