铜咔咯催化烯丙基sp3-C—H键与羧酸的酯化反应

doi:10.6023/cjoc202101023

摘要/Abstract

研究了5,10,15-三(五氟苯基)咔咯铜配合物(CuTPFC)催化的烯丙基sp³杂化C—H键与羧酸的氧化交叉脱氢偶联反应(CDC). 该反应可以平稳地生成烯丙基酯, 且具有广泛的底物范围和良好的官能团耐受性. 克级实验中, 在催化剂的用量仅为0.01 mol%的情况下, 转换量(TON)可以达到5100, 表明目前的催化体系在烯丙基酯合成方面具有潜在的应用前景.

关键词: 铜, 咔咯, 交叉脱氢偶联, 烯丙基化合物, 催化

Copper 5,10,15-tris(pentafluorophenyl)corrole (CuTPFC) catalyzed oxidative cross dehydrogenative coupling (CDC) of allylic sp³-C—H bonds and acids had been investigated in a homogeneous system, which provided allylic esters smoothly. This reaction proceeded with broad substrate scope and good functional group tolerance. In a gram scale test, the turnover number (TON) reached 5100 at only 0.01 mol% catalyst loading, indicating the current catalytic system has potential uses in the allylic esters.

Key words: copper, corrole, cross dehydrogenative coupling, allylic compounds, catalysis

引用此文

田婉群, 李梦媛, 杨霜, 章浩, 刘海洋, 肖新颜. 铜咔咯催化烯丙基sp³-C—H键与羧酸的酯化反应[J]. 有机化学, 2021, 41(7): 2875-2884.

Wanqun Tian, Mengyuan Li, Shuang Yang, Hao Zhang, Haiyang Liu, Xinyan Xiao. Copper Corrole as an Efficient Catalyst for Esterification of Allylic sp³-C—H Bonds with Carboxylic Acids[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2875-2884.

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Entry	Catalyst (mol%)	Solvent	Oxidant	Yield^b/%	TON
1	CuTPFC (1.0)	Toluene	DTBP	47	47
2	CuTPFC (1.0)	CHCl₃	DTBP	36	36
3	CuTPFC (1.0)	MeOH	DTBP	20	20
4	CuTPFC (1.0)	CH₃CN	DTBP	Trace	—
5	CuTPFC (1.0)	THF	DTBP	N.D.^c	—
6	CuTPFC (1.0)	EA	DTBP	93	93
7	CuTPFC (1.0)	DCE	DTBP	95	95
8	CuTPFC (0.5)	DCE	DTBP	94	188
9	CuTPFC (0.1)	DCE	DTBP	97 (95^d)	970
10	CuTPFC (0.01)	DCE	DTBP	75	7500
11	CuTPFC (0.1)	DCE	TBHP	87	870
12	CuTPFC (0.1)	DCE	m-CPBA	15	150
13	CuTPFC (0.1)	DCE	H₂O₂	17	170
14	CuTPFC (0.1)	DCE	DDQ	N.D.^c	—
15	MnTPFC (0.1)	DCE	DTBP	9	90
16	CoTPFC (0.1)^e	DCE	DTBP	15	150
17	CuTPC (0.1)	DCE	DTBP	91	910
18	Cu(OAc)₂ (0.1)	DCE	DTBP	23	230
19	CuOAc (0.1)	DCE	DTBP	84	840
20	—	DCE	DTBP	10	—

Entry	Catalyst (mol%)	Solvent	Oxidant	Yield^b/%	TON
1	CuTPFC (1.0)	Toluene	DTBP	47	47
2	CuTPFC (1.0)	CHCl₃	DTBP	36	36
3	CuTPFC (1.0)	MeOH	DTBP	20	20
4	CuTPFC (1.0)	CH₃CN	DTBP	Trace	—
5	CuTPFC (1.0)	THF	DTBP	N.D.^c	—
6	CuTPFC (1.0)	EA	DTBP	93	93
7	CuTPFC (1.0)	DCE	DTBP	95	95
8	CuTPFC (0.5)	DCE	DTBP	94	188
9	CuTPFC (0.1)	DCE	DTBP	97 (95^d)	970
10	CuTPFC (0.01)	DCE	DTBP	75	7500
11	CuTPFC (0.1)	DCE	TBHP	87	870
12	CuTPFC (0.1)	DCE	m-CPBA	15	150
13	CuTPFC (0.1)	DCE	H₂O₂	17	170
14	CuTPFC (0.1)	DCE	DDQ	N.D.^c	—
15	MnTPFC (0.1)	DCE	DTBP	9	90
16	CoTPFC (0.1)^e	DCE	DTBP	15	150
17	CuTPC (0.1)	DCE	DTBP	91	910
18	Cu(OAc)₂ (0.1)	DCE	DTBP	23	230
19	CuOAc (0.1)	DCE	DTBP	84	840
20	—	DCE	DTBP	10	—

铜咔咯催化烯丙基sp³-C—H键与羧酸的酯化反应

Copper Corrole as an Efficient Catalyst for Esterification of Allylic sp³-C—H Bonds with Carboxylic Acids

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Entry	Catalyst	DTBP (equiv.)	Yield/%		Sum/%
Entry	Catalyst	DTBP (equiv.)	5a	3a	Sum/%
1	—	—	26	19	45
2	—	2	28	19	47
3	CuTPFC	—	10	42	52
4	CuTPFC	2	17	46	63
5	CuTPFC	4	16	49	65

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