钌选择性催化烯丙醇无受体脱氢合成α,β-不饱和羰基化合物

doi:10.6023/cjoc202107037

有机化学 ›› 2021, Vol. 41 ›› Issue (11): 4361-4369.DOI: 10.6023/cjoc202107037 上一篇下一篇

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研究论文

钌选择性催化烯丙醇无受体脱氢合成α,β-不饱和羰基化合物

刘嘉豪^a, 张世冬^a, 栾自鸿^a, 刘艳^b, 柯卓锋^a^,^*()

a 中山大学材料科学与工程学院聚合物复合材料及功能材料教育部重点实验室广州 510006
b 广东工业大学轻工化工学院广州 510006

收稿日期:2021-07-16 修回日期:2021-08-15 发布日期:2021-08-24
通讯作者: 柯卓锋
作者简介:
† 共同第一作者.
基金资助:
国家自然科学基金(21973113); 国家自然科学基金(21977019); 广东省自然科学杰出青年基金(2015A030306027)

Ruthenium Catalyzed Selective Acceptorless Dehydrogenation of Allylic Alcohols to α,β-Unsaturated Carbonyls

Jiahao Liu^a, Shidong Zhang^a, Zihong Luan^a, Yan Liu^b, Zhuofeng Ke^a()

a Key Laboratory for Polymeric Composite & Functional Materials of Ministry of Education, School of Materials Science and Engineering, Sun Yat-sen University, Guangzhou 510006
b School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006

Received:2021-07-16 Revised:2021-08-15 Published:2021-08-24
Contact: Zhuofeng Ke
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21973113); National Natural Science Foundation of China(21977019); Guangdong Natural Science Funds for Distinguished Young Scholar(2015A030306027)

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摘要/Abstract

过渡金属催化烯丙醇的选择性脱氢氧化以得到相应的α,β-不饱和羰基化合物在最近广受关注, 但是很多方法需要用到化学计量的氧化剂, 这会带来大量的废弃副产物, 原子经济性不足. 本工作开发了一种简单易得的[RuCl₂(p- cymene)]₂催化系统, 可用于高效地催化烯丙醇选择性脱氢合成α,β-不饱和羰基化合物, 而无需使用额外的氧化剂或H₂受体.

关键词: 钌, 无受体脱氢, 烯丙醇, α,β-不饱和羰基化合物

Transition metal-catalyzed allyllic alcohol selective dehydrogenation to generate the corresponding α,β-unsaturated carbonyl compound has attached great attention. However, most of these methods require stoichiometric quantities of oxidants, which will bring a lot of by-products and lack of atomic economy. Herein, a simple [RuCl₂(p-cymene)]₂ catalyzed system to efficiently catalyze the selective dehydrogenation of allyl alcohol to form α,β-unsaturated carbonyls without the use of additional oxidants or H₂ acceptors has been developed.

Key words: ruthenium, acceptorless dehydrogenation, allylic alcohols, α,β-unsaturated carbonyls

引用此文

刘嘉豪, 张世冬, 栾自鸿, 刘艳, 柯卓锋. 钌选择性催化烯丙醇无受体脱氢合成α,β-不饱和羰基化合物[J]. 有机化学, 2021, 41(11): 4361-4369.

Jiahao Liu, Shidong Zhang, Zihong Luan, Yan Liu, Zhuofeng Ke. Ruthenium Catalyzed Selective Acceptorless Dehydrogenation of Allylic Alcohols to α,β-Unsaturated Carbonyls[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4361-4369.

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钌选择性催化烯丙醇无受体脱氢合成α,β-不饱和羰基化合物

Ruthenium Catalyzed Selective Acceptorless Dehydrogenation of Allylic Alcohols to α,β-Unsaturated Carbonyls

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Entry	Additive	Solvent	T/℃	t/h	Yield^b/%
1	—	t-AmOH	100	24	Trace
2^c	Cu(OAc)₂•H₂O	t-AmOH	100	16	93
3^d	Cu(OAc)₂•H₂O	t-AmOH	100	16	93
4	Cu(OAc)₂•H₂O	t-AmOH	100	16	93
5^e	Cu(OAc)₂•H₂O	t-AmOH	100	36	71
6	Cu(OAc)₂•H₂O	t-AmOH	80	36	91
7	Cu(OAc)₂•H₂O	t-AmOH	60	48	Trace
8	Cu(OAc)₂•H₂O	t-AmOH	r.t.	72	Trace
9	AgOAc	t-AmOH	100	16	14^f
10	KOAc	t-AmOH	100	48	85
11	NaOAc	t-AmOH	100	36	72
12	Na₂CO₃	t-AmOH	100	16	76
13	Cu(OTf)₂	t-AmOH	100	84	58
14	Cu(OAc)₂•H₂O	Toluene	100	84	68
15	Cu(OAc)₂•H₂O	EtOH	80	48	Trace
16	Cu(OAc)₂•H₂O	H₂O	100	48	Trace

Entry	Substrate	Product	Yield^b/%
1			93
2			93
3			94
4			91
5			93
6			93
7			94
8			95
9			92
Entry	Substrate	Product	Yield^b/%
10			93
11			90
12			94
13			93
14			92
15			90

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