Abstract

Magnesium carbenoids are a class of organomagnesium species possessing a halo group at the α-position. The reactions of magnesium carbenoids can be classified into the following three categories: nucleophilic reactions resembling Grignard reagents, electrophilic reactions resembling organic halides, and rearrangements resembling carbenes. This short review summarizes recent studies on magnesium carbenoids reported between 2010 and 2016, and milestone studies reported before 2010 according to the classification of the reactions into the aforementioned three categories.

1 Introduction

2 Structures of Magnesium Carbenoids

3 Reactions of Magnesium Carbenoids as Nucleophiles

3.1 Nucleophilic Reactions of Magnesium Carbenoids

3.2 Nucleophilic Reactions of Magnesium Alkylidene Carbenoids

3.3 Nucleophilic Reactions of Cyclopropylmagnesium Carbenoids

4 Electrophilic Reactions of Magnesium Carbenoids

4.1 Reactions with Nucleophiles Followed by Electrophiles

4.2 Reactions with Nucleophiles Possessing Electrophilic Functional Groups

4.3 Nucleophilic Substitution Followed by β-Elimination

5 Rearrangements of Magnesium Carbenoids

5.1 1,2-Shifts of Magnesium Carbenoids

5.2 1,3-C–H Insertions of Magnesium Carbenoids

5.3 1,5-C–H Insertions of Magnesium Carbenoids

5.4 [2+1] Cycloaddition of a Magnesium Carbenoid

6 Conclusion and Outlook

Magnesium carbenoids are a class of organomagnesium species possessing a halo group at the α-position. The reactions of magnesium carbenoids can be classified into the following three categories: nucleophilic reactions resembling Grignard reagents, electrophilic reactions resembling organic halides, and rearrangements resembling carbenes. This short review summarizes recent studies on magnesium carbenoids reported between 2010 and 2016, and milestone studies reported before 2010 according to the classification of the reactions into the aforementioned three categories.

1 Introduction

2 Structures of Magnesium Carbenoids

3 Reactions of Magnesium Carbenoids as Nucleophiles

3.1 Nucleophilic Reactions of Magnesium Carbenoids

3.2 Nucleophilic Reactions of Magnesium Alkylidene Carbenoids

3.3 Nucleophilic Reactions of Cyclopropylmagnesium Carbenoids

4 Electrophilic Reactions of Magnesium Carbenoids

4.1 Reactions with Nucleophiles Followed by Electrophiles

4.2 Reactions with Nucleophiles Possessing Electrophilic Functional Groups

4.3 Nucleophilic Substitution Followed by β-Elimination

5 Rearrangements of Magnesium Carbenoids

5.1 1,2-Shifts of Magnesium Carbenoids

5.2 1,3-C–H Insertions of Magnesium Carbenoids

5.3 1,5-C–H Insertions of Magnesium Carbenoids

5.4 [2+1] Cycloaddition of a Magnesium Carbenoid

6 Conclusion and Outlook

中文翻译：

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镁类胡萝卜素化学的最新进展

摘要

镁类胡萝卜素是一类在α位置具有卤素基团的有机镁物质。类镁镁的反应可分为以下三类：类似于格利雅试剂的亲核反应，类似于有机卤化物的亲电反应和类似于碳烯的重排。这篇简短的综述根据对上述三类反应的分类，总结了最近在2010年至2016年间报道的关于镁类类胡萝卜素的研究，以及在2010年之前报道的里程碑式研究。

1引言

2镁类胡萝卜素的结构

3镁类胡萝卜素作为亲核试剂的反应

3.1镁类胡萝卜素的亲核反应

3.2镁亚烷基类胡萝卜素的亲核反应

3.3环丙基镁类胡萝卜素的亲核反应

4镁类胡萝卜素的亲电反应

4.1与亲核试剂的反应，随后是亲电试剂

4.2与具有亲电子官能团的亲核试剂的反应

4.3亲核取代，然后消除β

5镁类胡萝卜素的重排

5.1镁类胡萝卜素的1,2-移位

5.2 1,3-C–H镁类胡萝卜素插入

5.3 1,5-C–H镁类胡萝卜素插入

5.4 [2 + 1]镁类胡萝卜素的环加成

6结论与展望

镁类胡萝卜素是一类在α位置具有卤素基团的有机镁物质。类镁镁的反应可分为以下三类：类似于格利雅试剂的亲核反应，类似于有机卤化物的亲电反应和类似于碳烯的重排。这篇简短的综述根据对上述三类反应的分类，总结了最近在2010年至2016年间报道的关于镁类类胡萝卜素的研究，以及在2010年之前报道的里程碑式研究。

1引言

2镁类胡萝卜素的结构

3镁类胡萝卜素作为亲核试剂的反应

3.1镁类胡萝卜素的亲核反应

3.2镁亚烷基类胡萝卜素的亲核反应

3.3环丙基镁类胡萝卜素的亲核反应

4镁类胡萝卜素的亲电反应

4.1与亲核试剂的反应，随后是亲电试剂

4.2与具有亲电子官能团的亲核试剂的反应

4.3亲核取代，然后消除β

5镁类胡萝卜素的重排

5.1镁类胡萝卜素的1,2-移位

5.2 1,3-C–H镁类胡萝卜素插入

5.3 1,5-C–H镁类胡萝卜素插入

5.4 [2 + 1]镁类胡萝卜素的环加成

6结论与展望