电化学介导羧酸与醇的酯化反应

doi:10.6023/cjoc202302004

摘要/Abstract

通过电化学介导羧酸和醇反应合成了一系列酯类化合物. 该策略通过温和绿色的电化学合成方式进行, 反应在室温下即可发生, 无需惰性气体保护, 过程中也无需使用强酸和金属催化剂等进行辅助催化. 反应在无隔膜电解槽中以恒流模式进行, 以较高的收率生成酯化产物. 相比有机试剂促进的酯化反应, 该方案不残留需柱层析分离的副产物, 可适用难于反应的叔丁醇.

关键词: 电化学介导, 酯化反应, 有机电合成

A series of esters were prepared by electrochemical synthesis of carboxylic acids with alcohols. This protocol can be carried out at room temperature without inert atmosphere, strong acids or metal catalysts, etc. The esterification reaction processes in an undivided electrolytic cell with constant current mode and the esterification products are generated in good yields. Compared with esterification promoted by organic reagents, this protocol avoids the byproducts which have to be separated by column chromatography and successful for tertiary alcohol which is generally difficult to undergo esterification directly, providing a new access to the esterification of carboxylic acids and alcohols.

Key words: electrochemical mediation, esterification reaction, electromechanical synthesis

引用此文

钟赟哲, 陈颖, 俞磊, 周宏伟. 电化学介导羧酸与醇的酯化反应[J]. 有机化学, 2023, 43(8): 2855-2863.

Yunzhe Zhong, Ying hen, Lei Yu, Hongwei Zhou. Electrochemical Mediated Esterification Reaction of Carboxylic Acids and Alcohols[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2855-2863.

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Entry	Additive	Solvent	Current/mA	Electrode	Yield^b/%
1^c	TBAB/Na₂S₂O₅	EtOH	5	Graphite (＋)/Pt(－)	54
2^d	TBAB/Na₂S₂O₅	EtOH	10	Graphite (＋)/Pt(－)	86
3^e	TBAB/Na₂S₂O₅	EtOH	15	Graphite (＋)/Pt(－)	84
4	KBr/Na₂S₂O₅	EtOH	10	Graphite (＋)/Pt(－)	25
5	KCl/Na₂S₂O₅	EtOH	10	Graphite (＋)/Pt(－)	NR
6	TBAB/Na₂S₂O₅	CH₃CN	10	Graphite (＋)/Pt(－)	56
7	TBAB/Na₂S₂O₅	DMF	10	Graphite (＋)/Pt(－)	47
8	TBAB/Na₂S₂O₅	DCE	10	Graphite (＋)/Pt(－)	37
9	TBAB/Na₂S₂O₅	Acetone	10	Graphite (＋)/Pt(－)	83
10	TBAB/Na₂S₂O₅	EtOH	10	Graphite (＋)/Graphite (－)	48
11	TBAB/Na₂S₂O₅	EtOH	10	Glassy carbon (＋)/Pt(－)	62
12	TBAB/Na₂S₂O₅	EtOH	10	Pt (＋)/Pt(－)	NR
13^f	TBAB/Na₂S₂O₅	EtOH	—	Graphite (＋)/Pt(－)	NR
14^g	TBAB	EtOH	10	Graphite (＋)/Pt(－)	NR
15^h	TBAB/Na₂S₂O₅	EtOH	10	Graphite (＋)/Pt(－)	76

Entry	Additive	Solvent	Current/mA	Electrode	Yield^b/%
1^c	TBAB/Na₂S₂O₅	EtOH	5	Graphite (＋)/Pt(－)	54
2^d	TBAB/Na₂S₂O₅	EtOH	10	Graphite (＋)/Pt(－)	86
3^e	TBAB/Na₂S₂O₅	EtOH	15	Graphite (＋)/Pt(－)	84
4	KBr/Na₂S₂O₅	EtOH	10	Graphite (＋)/Pt(－)	25
5	KCl/Na₂S₂O₅	EtOH	10	Graphite (＋)/Pt(－)	NR
6	TBAB/Na₂S₂O₅	CH₃CN	10	Graphite (＋)/Pt(－)	56
7	TBAB/Na₂S₂O₅	DMF	10	Graphite (＋)/Pt(－)	47
8	TBAB/Na₂S₂O₅	DCE	10	Graphite (＋)/Pt(－)	37
9	TBAB/Na₂S₂O₅	Acetone	10	Graphite (＋)/Pt(－)	83
10	TBAB/Na₂S₂O₅	EtOH	10	Graphite (＋)/Graphite (－)	48
11	TBAB/Na₂S₂O₅	EtOH	10	Glassy carbon (＋)/Pt(－)	62
12	TBAB/Na₂S₂O₅	EtOH	10	Pt (＋)/Pt(－)	NR
13^f	TBAB/Na₂S₂O₅	EtOH	—	Graphite (＋)/Pt(－)	NR
14^g	TBAB	EtOH	10	Graphite (＋)/Pt(－)	NR
15^h	TBAB/Na₂S₂O₅	EtOH	10	Graphite (＋)/Pt(－)	76