Palladium-Catalyzed Regioselective Aryl Phenoxylation of Allenamide

doi:10.6023/cjoc202309003

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (1): 224-231.DOI: 10.6023/cjoc202309003 Previous Articles Next Articles

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钯催化联烯胺区域选择性芳基酚氧化反应

孟宪强^a^,^b, 杨艺^a, 梁万洁^b, 王靖涛^c, 张荣葵^d^,^*(), 刘会^a^,^c^,^d^,^*()

a 山东理工大学化学化工学院山东淄博 255049
b 山东安得医疗用品股份有限公司山东淄博 255086
c 天津大学化工学院天津 300072
d 淄博市中心医院无菌供应中心山东淄博 255020

收稿日期:2023-09-04 修回日期:2023-09-12 发布日期:2024-01-31
基金资助:
国家自然科学基金(22078178)

Palladium-Catalyzed Regioselective Aryl Phenoxylation of Allenamide

Xianqiang Meng^a^,^b, Yi Yang^a, Wanjie Liang^b, Jingtao Wang^c, Rongkui Zhang^d(), Hui Liu^a^,^c^,^d()

a School of Chemistry & Chemical Engineering, Shandong University of Technology, Zibo, Shandong 255049
b Shandong Ande Healthcare Apparatus Co., Ltd., Zibo, Shandong 255086
c School of Chemical Engineering, Tianjin University, Tianjin 300072
d Central Sterile Supply Department, Zibo Central Hospital, Zibo, Shandong 255020

Received:2023-09-04 Revised:2023-09-12 Published:2024-01-31
Contact: *E-mail: huiliu1030@163.com; E-mail: 1508364771@qq.com
Supported by:
National Natural Science Foundation of China(22078178)

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Abstract

A palladium-catalyzed regioselective aryl phenoxylation of allenamide with phenol derivatives has been developed, providing valuable branched allyl ether products in moderate to excellent yields under mild reaction conditions. Importantly, only the proximal addition products of allenamide were observed in the reaction process, and no distal addition products were observed. A coordinated palladium complex was proposed to be responsible for the excellent proximal addition in the insertion step. The final nucleophilic attack at α-position was induced by the steric effect of palladium complex.

Key words: palladium-catalysis, proximal addition, aryl phenoxylation

Cite this article

Xianqiang Meng, Yi Yang, Wanjie Liang, Jingtao Wang, Rongkui Zhang, Hui Liu. Palladium-Catalyzed Regioselective Aryl Phenoxylation of Allenamide[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 224-231.

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References 18

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Entry	Catalyst	Ligand	Base	Solvent	Time/h	Yield^b/%
1	Pd(PPh₃)₄	—	Cy₂NMe	MeCN	3	20
2	Pd(PPh₃)₄	—	K₂CO₃	MeCN	3	46
3	Pd(PPh₃)₄	—	Cs₂CO₃	MeCN	3	40
4	PdCl₂(dppf)	PPh₃	K₂CO₃	MeCN	3	38
5	Pd₂(dba)₃	PPh₃	K₂CO₃	MeCN	3	43
6	Pd(dba)₂	PPh₃	K₂CO₃	MeCN	3	44
7	Pd(dba)₂	dppm	K₂CO₃	MeCN	3	46
8	Pd(dba)₂	PCy₃	K₂CO₃	MeCN	3	54
9	Pd(dba)₂	P(2-furyl)₃	K₂CO₃	MeCN	3	57
10	Pd(dba)₂	P(2-furyl)₃	K₂CO₃	THF	3	19
11	Pd(dba)₂	P(2-furyl)₃	K₂CO₃	DMF	3	60
12^c	Pd(dba)₂	P(2-furyl)₃	K₂CO₃	DMF	3	65
13^c	Pd(dba)₂	P(2-furyl)₃	K₂CO₃	DMF	2	71

Entry	Catalyst	Ligand	Base	Solvent	Time/h	Yield^b/%
1	Pd(PPh₃)₄	—	Cy₂NMe	MeCN	3	20
2	Pd(PPh₃)₄	—	K₂CO₃	MeCN	3	46
3	Pd(PPh₃)₄	—	Cs₂CO₃	MeCN	3	40
4	PdCl₂(dppf)	PPh₃	K₂CO₃	MeCN	3	38
5	Pd₂(dba)₃	PPh₃	K₂CO₃	MeCN	3	43
6	Pd(dba)₂	PPh₃	K₂CO₃	MeCN	3	44
7	Pd(dba)₂	dppm	K₂CO₃	MeCN	3	46
8	Pd(dba)₂	PCy₃	K₂CO₃	MeCN	3	54
9	Pd(dba)₂	P(2-furyl)₃	K₂CO₃	MeCN	3	57
10	Pd(dba)₂	P(2-furyl)₃	K₂CO₃	THF	3	19
11	Pd(dba)₂	P(2-furyl)₃	K₂CO₃	DMF	3	60
12^c	Pd(dba)₂	P(2-furyl)₃	K₂CO₃	DMF	3	65
13^c	Pd(dba)₂	P(2-furyl)₃	K₂CO₃	DMF	2	71

钯催化联烯胺区域选择性芳基酚氧化反应

Palladium-Catalyzed Regioselective Aryl Phenoxylation of Allenamide

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