N-Heterocyclic Carbene (NHC)/Ag(I) Co-catalyzed Synthesis of 2-Oxo-2-arylethyl Aryl Formates

doi:10.6023/cjoc202008035

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1607-1613.DOI: 10.6023/cjoc202008035 Previous Articles Next Articles

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氮杂环卡宾(NHC)/银(I)共催化合成2-氧代-2-芳乙基芳甲酸酯

成立¹, 王文蓉¹, 孙玉倩¹, 李团结¹^,^* ltj2008@jsnu.edu.cn., 于晨侠¹, 姚昌盛¹^,^*()

1 江苏师范大学化学与材料科学学院江苏省功能材料绿色合成重点实验室江苏徐州 221116

收稿日期:2020-08-20 修回日期:2020-10-13 发布日期:2020-12-24
通讯作者: 李团结, 姚昌盛
基金资助:
国家自然科学基金(2177020721); 国家自然科学基金(21871113); 江苏高等学校自然科学基金(17KJA150003)

N-Heterocyclic Carbene (NHC)/Ag(I) Co-catalyzed Synthesis of 2-Oxo-2-arylethyl Aryl Formates

Li Cheng¹, Wenrong Wang¹, Yuqian Sun¹, Tuanjie Li¹^,^* ltj2008@jsnu.edu.cn., Chenxia Yu¹, Changsheng Yao¹^,^*()

1 Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116

Received:2020-08-20 Revised:2020-10-13 Published:2020-12-24
Contact: Tuanjie Li, Changsheng Yao
About author:
* Corresponding authors. E-mail: csyao@jsnu.edu.cn;
E-mail: ltj2008@jsnu.edu.cn.
Supported by:
National Science Foundation of China(2177020721); National Science Foundation of China(21871113); Natural Science Foundation of the Jiangsu Higher Education Institution(17KJA150003)

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Abstract

An N-heterocyclic carbene (NHC)/Ag(I) co-catayzed efficient synthesis of 2-oxo-2-arylethyl aryl formates was realized by the reaction of aryl aldehydes with (bromoethynyl)benzenes. This method features broad substrate scope, ready availability of starting materials and operational simplicity, which gives an alternative access to α-acyloxycarbonyl derivatives.

Key words: N-heterocyclic carbene (NHC), Ag(I), co-catalysis, α-acyloxycarbonyl derivatives

Cite this article

Li Cheng, Wenrong Wang, Yuqian Sun, Tuanjie Li, Chenxia Yu, Changsheng Yao. N-Heterocyclic Carbene (NHC)/Ag(I) Co-catalyzed Synthesis of 2-Oxo-2-arylethyl Aryl Formates[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1607-1613.

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Fig. & Tab. 5

References 31

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Entry	NHC	Base	Solvent	T/℃	Yield^b/%
1	4	K₂CO₃	DCM	80	10
2	5	K₂CO₃	DCM	80	0
3	6	K₂CO₃	DCM	80	45
4	7	K₂CO₃	DCM	80	60
5	7	K₂CO₃	K₂CO₃	80	52
6	7	K₂CO₃	K₂CO₃	80	15
7	7	K₂CO₃	K₂CO₃	80	14
8	7	K₂CO₃	K₂CO₃	80	8
9	7	K₃PO₄	DCM	80	52
10	7	DBU	DCM	80	0
11	7	DABCO	DCM	80	0
12	7	Cs₂CO₃	DCM	80	10
13	7	K₂CO₃	DCM	30	0
14	7	K₂CO₃	DCM	40	10
15	7	K₂CO₃	DCM	50	47
16	7	K₂CO₃	DCM	60	59
17	7	K₂CO₃	DCM	70	70

Entry	NHC	Base	Solvent	T/℃	Yield^b/%
1	4	K₂CO₃	DCM	80	10
2	5	K₂CO₃	DCM	80	0
3	6	K₂CO₃	DCM	80	45
4	7	K₂CO₃	DCM	80	60
5	7	K₂CO₃	K₂CO₃	80	52
6	7	K₂CO₃	K₂CO₃	80	15
7	7	K₂CO₃	K₂CO₃	80	14
8	7	K₂CO₃	K₂CO₃	80	8
9	7	K₃PO₄	DCM	80	52
10	7	DBU	DCM	80	0
11	7	DABCO	DCM	80	0
12	7	Cs₂CO₃	DCM	80	10
13	7	K₂CO₃	DCM	30	0
14	7	K₂CO₃	DCM	40	10
15	7	K₂CO₃	DCM	50	47
16	7	K₂CO₃	DCM	60	59
17	7	K₂CO₃	DCM	70	70

Entry	R	Ar	Time/h	Product	Yield/%
1	4-ClC₆H₄	C₆H₅	12	3a	70
2	4-BrC₆H₄	C₆H₅	12	3b	68
3	4-FC₆H₄	C₆H₅	12	3c	58
4	3-BrC₆H₄	C₆H₅	12	3d	65
5	3,4-Cl₂C₆H₃	C₆H₅	12	3e	75
6	4-O₂NC₆H₄	C₆H₅	12	3f	74
7	4-CH₃OC₆H₄	C₆H₅	24	3g	48
8	Thiophene-2-yl	C₆H₅	12	3h	58
9	3,4-Cl₂C₆H₃	4-ClC₆H₄	12	3i	73
10	4-ClC₆H₄	4-ClC₆H₄	12	3j	68
11	4-NO₂C₆H₄	4-ClC₆H₄	12	3k	76
12	4-CH₃OC₆H₄	4-ClC₆H₄	24	3l	50
13	Thiophene-2-yl	4-ClC₆H₄	12	3m	62
14	3,4-Cl₂C₆H₃	4-CH₃CH₂C₆H₄	12	3n	70
15	4-CH₃OC₆H₄	4-CH₃CH₂C₆H₄	24	3o	45
16	Thiophene-2-yl	4-CH₃CH₂C₆H₄	12	3p	60

Entry	R	Ar	Time/h	Product	Yield/%
1	4-ClC₆H₄	C₆H₅	12	3a	70
2	4-BrC₆H₄	C₆H₅	12	3b	68
3	4-FC₆H₄	C₆H₅	12	3c	58
4	3-BrC₆H₄	C₆H₅	12	3d	65
5	3,4-Cl₂C₆H₃	C₆H₅	12	3e	75
6	4-O₂NC₆H₄	C₆H₅	12	3f	74
7	4-CH₃OC₆H₄	C₆H₅	24	3g	48
8	Thiophene-2-yl	C₆H₅	12	3h	58
9	3,4-Cl₂C₆H₃	4-ClC₆H₄	12	3i	73
10	4-ClC₆H₄	4-ClC₆H₄	12	3j	68
11	4-NO₂C₆H₄	4-ClC₆H₄	12	3k	76
12	4-CH₃OC₆H₄	4-ClC₆H₄	24	3l	50
13	Thiophene-2-yl	4-ClC₆H₄	12	3m	62
14	3,4-Cl₂C₆H₃	4-CH₃CH₂C₆H₄	12	3n	70
15	4-CH₃OC₆H₄	4-CH₃CH₂C₆H₄	24	3o	45
16	Thiophene-2-yl	4-CH₃CH₂C₆H₄	12	3p	60

氮杂环卡宾(NHC)/银(I)共催化合成2-氧代-2-芳乙基芳甲酸酯

N-Heterocyclic Carbene (NHC)/Ag(I) Co-catalyzed Synthesis of 2-Oxo-2-arylethyl Aryl Formates

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