镍催化芳基碳酸酯和芳基氨基磺酸酯与环烯烃的Heck反应

doi:10.6023/cjoc202204034

摘要/Abstract

报道了一种高效的镍催化芳基碳酸酯和芳基氨基磺酸酯的惰性C—O键与环烯烃的Heck反应. 带有各种官能团的萘基、杂环以及苯基碳酸酯均能在由二价镍、PhBPE配体和还原性金属锌组成的催化体系中顺利反应.

An efficient nickel-catalyzed Heck reaction of cycloalkenes with inert C—O bonds of aryl carbonates and sulfamates has been developed. Naphthyl, heterocycles and simple phenyl substituted carbonates with various functional groups are compatible with the catalytic systems comprising Ni(II), PhBPE ligand and reductive metal Zn.

Key words: nickel, Heck reaction, aryl carbonates, aryl sulfamates

引用此文

曾旭群, 张倩, 吴旭枫, 张静枫, 张鑫伟, 黄晓雷. 镍催化芳基碳酸酯和芳基氨基磺酸酯与环烯烃的Heck反应[J]. 有机化学, 2022, 42(9): 2981-2987.

Xuqun Zeng, Qian Zhang, Xufeng Wu, Jingfeng Zhang, Xinwei Zhang, Xiaolei Huang. Nickel-Catalyzed Heck Reaction of Cycloalkenes with Inert C—O Bonds of Aryl Carbonates and Aryl Sulfamates[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2981-2987.

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图/表 5

Scheme 1. Evolution of transition metal-catalyzed cross-coupling of inert C—O bonds of aryl carbonates

Entry	Reductive metal	Solvent	T/°C	Yield^b/%
1	Zn	DMF	100	85
2^c	Zn	DMF	100	40
3^d	Zn	DMF	100	68
4	Mn	DMF	100	0
5	Mg	DMF	100	0
6	Fe	DMF	100	0
7	Zn	Dioxane	100	0
8	Zn	Toluene	100	0
9	Zn	DCE	100	0
10	Zn	DMSO	100	64
11	Zn	DMA	100	72
12	Zn	DMF	90	36
13	Zn	DMF	110	64
14	Zn	DMF	120	62

Table 1. Optimization of reaction conditionsa

Table 2. Scope of aryl carbonates with cycloalkenesa

Table 3. Scope of aryl sulfamatesa

Scheme 2. Proposed mechanisms

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