Iron-Catalyzed Decarboxylative Heck-Type Alkylation of Conjugate 1,3-Dienes

doi:10.6023/cjoc202103029

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2707-2714.DOI: 10.6023/cjoc202103029 Previous Articles Next Articles

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铁催化1,3-共轭烯烃的Heck型脱羧烷基化反应

王凯凯^a, 陈绍维^b, 李亚军^b, 李达谅^a^,^*(), 鲍红丽^b^,^*()

a 福建师范大学南方生物医学研究中心&化学与材料学院福州 350007
b 中国科学院福建物质结构研究所煤制乙二醇重点实验室福州 350002

收稿日期:2021-03-18 修回日期:2021-04-15 发布日期:2021-04-29
通讯作者: 李达谅, 鲍红丽
基金资助:
国家自然科学基金(21871258); 国家自然科学基金(21922112); 国家自然科学基金(22001251); 福建师范大学校创新团队(IRTL1703)

Iron-Catalyzed Decarboxylative Heck-Type Alkylation of Conjugate 1,3-Dienes

Kaikai Wang^a, Shaowei Chen^b, Yajun Li^b, Daliang Li^a(), Hongli Bao^b()

a Biomedical Research Center of South China & College of Chemistry and Materials Science, Fujian Normal University, Fuzhou 350007
b Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002

Received:2021-03-18 Revised:2021-04-15 Published:2021-04-29
Contact: Daliang Li, Hongli Bao
Supported by:
National Natural Science Foundation of China(21871258); National Natural Science Foundation of China(21922112); National Natural Science Foundation of China(22001251); Innovative Research Teams Program of Fujian Normal University(IRTL1703)

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Abstract

An iron-catalyzed decarboxylative Heck-type alkylation of conjugate 1,3-dienes with alkyl diacyl peroxides andt-butyl peresters is reported. This method offers an efficient approach to alkylation of 1,3-dienes with good yields, and in some cases with high selectivities. Late-stage alkylation of bioactive compounds was also found to be effective.

Key words: iron catalysis, 1,3-dienes, Heck-type alkylation, decarboxylation, peresters, diacyl peroxides

Cite this article

Kaikai Wang, Shaowei Chen, Yajun Li, Daliang Li, Hongli Bao. Iron-Catalyzed Decarboxylative Heck-Type Alkylation of Conjugate 1,3-Dienes[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2707-2714.

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References 13

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Entry	Catalyst	Solvent	Temp/℃	Yield^b/%
1	Fe(OTs)₃	THF	80	40 (2∶1)
2	Mn(OAc)₂	THF	80	Trace
3	MnBr₂	THF	80	Trace
4	MnCl₂•4H₂O	THF	80	Trace
5	Ni(acac)₂	THF	80	Trace
6	CoBr₂	THF	80	Trace
7	CuBr	THF	80	4
8	Fe(acac)₃	THF	80	4
9	FeCl₂	THF	80	10
10	Fe(OTf)₃	THF	80	67 (2∶1)
11	Fe(OTf)₃	THF	60	65 (2∶1)
12	Fe(OTf)₃	THF	70	60 (2∶1)
13	Fe(OTf)₃	THF	90	63 (2∶1)
14	Fe(OTf)₃	THF	100	64 (2∶1)
15	Fe(OTf)₃	THF	80	74 (2∶1)^c

Entry	Catalyst	Solvent	Temp/℃	Yield^b/%
1	Fe(OTs)₃	THF	80	40 (2∶1)
2	Mn(OAc)₂	THF	80	Trace
3	MnBr₂	THF	80	Trace
4	MnCl₂•4H₂O	THF	80	Trace
5	Ni(acac)₂	THF	80	Trace
6	CoBr₂	THF	80	Trace
7	CuBr	THF	80	4
8	Fe(acac)₃	THF	80	4
9	FeCl₂	THF	80	10
10	Fe(OTf)₃	THF	80	67 (2∶1)
11	Fe(OTf)₃	THF	60	65 (2∶1)
12	Fe(OTf)₃	THF	70	60 (2∶1)
13	Fe(OTf)₃	THF	90	63 (2∶1)
14	Fe(OTf)₃	THF	100	64 (2∶1)
15	Fe(OTf)₃	THF	80	74 (2∶1)^c

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铁催化1,3-共轭烯烃的Heck型脱羧烷基化反应

Iron-Catalyzed Decarboxylative Heck-Type Alkylation of Conjugate 1,3-Dienes

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