Palladium-Catalyzed Regioselective ortho-Acylation of Azoxybenzenes under Aqueous Conditions

doi:10.6023/cjoc201905017

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3176-3182.DOI: 10.6023/cjoc201905017 Previous Articles Next Articles

在水相中钯催化氧化偶氮苯的区域选择性邻位酰基化反应

陈晓培*(), 马志伟, 王川川, 刘俊桃, 吴金松

河南牧业经济学院理学部郑州 450046 Faculty of Science, Henan University of Animal Husbandry and Economy, Zhengzhou 450046

收稿日期:2019-05-09 发布日期:2019-07-09
通讯作者: 陈晓培 E-mail:chenxp@hnuahe.edu.cn
基金资助:
河南省高等学校重点科研项目计划(20A150019);河南牧业经济学院博士科研启动资金(53000168)

Palladium-Catalyzed Regioselective ortho-Acylation of Azoxybenzenes under Aqueous Conditions

Chen Xiaopei*(), Ma Zhiwei, Wang Chuanchuan, Liu Juntao, Wu Jinsong

Received:2019-05-09 Published:2019-07-09
Contact: Chen Xiaopei E-mail:chenxp@hnuahe.edu.cn
Supported by:
the Key Scientific Research Project for Colleges and Universities of Henan Province(20A150019);the Doctoral Research Startup Fund of Henan University of Animal Husbandry and Economy(53000168)

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Chen Xiaopei, Ma Zhiwei, Wang Chuanchuan, Liu Juntao, Wu Jinsong. Palladium-Catalyzed Regioselective ortho-Acylation of Azoxybenzenes under Aqueous Conditions[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3176-3182.

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References 20

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Entry^a	Catalyst	Oxidant	PTC	Yield ^b/%
1	PdCl₂	TBHP		15
2	PdCl₂	TBHP	SDS	35
3	Pd(TFA)₂	TBHP	SDS	68
4	Pd(OAc)₂	TBHP	SDS	80
5	Pd(OAc)₂	DBHP	SDS	20
6	Pd(OAc)₂	AgOAc	SDS	15
7	Pd(OAc)₂	K₂S₂O₈	SDS	Trace
8	Pd(OAc)₂	(NH₄)₂S₂O₈	SDS	Trace
9	Pd(OAc)₂	BQ	SDS	ND^e
10	Pd(OAc)₂	DDQ	SDS	ND^e
11	Pd(OAc)₂	H₂O₂	SDS	ND^e
12	Pd(OAc)₂	TBHP	TBAB	20
13	Pd(OAc)₂	TBHP	18-Crown-6	42
14	Pd(OAc)₂	TBHP	Tween 80	10
15^c	Pd(OAc)₂	TBHP	SDS	65
16^d	Pd(OAc)₂	TBHP	SDS	75


Entry^a	Catalyst	Oxidant	PTC	Yield ^b/%
1	PdCl₂	TBHP		15
2	PdCl₂	TBHP	SDS	35
3	Pd(TFA)₂	TBHP	SDS	68
4	Pd(OAc)₂	TBHP	SDS	80
5	Pd(OAc)₂	DBHP	SDS	20
6	Pd(OAc)₂	AgOAc	SDS	15
7	Pd(OAc)₂	K₂S₂O₈	SDS	Trace
8	Pd(OAc)₂	(NH₄)₂S₂O₈	SDS	Trace
9	Pd(OAc)₂	BQ	SDS	ND^e
10	Pd(OAc)₂	DDQ	SDS	ND^e
11	Pd(OAc)₂	H₂O₂	SDS	ND^e
12	Pd(OAc)₂	TBHP	TBAB	20
13	Pd(OAc)₂	TBHP	18-Crown-6	42
14	Pd(OAc)₂	TBHP	Tween 80	10
15^c	Pd(OAc)₂	TBHP	SDS	65
16^d	Pd(OAc)₂	TBHP	SDS	75

在水相中钯催化氧化偶氮苯的区域选择性邻位酰基化反应

Palladium-Catalyzed Regioselective ortho-Acylation of Azoxybenzenes under Aqueous Conditions

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