Trifluoromethyl Sulfonic Anhydride Mediated Addition of Pyridine with Ynamides

doi:10.6023/cjoc202203061

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (8): 2433-2437.DOI: 10.6023/cjoc202203061 Previous Articles Next Articles

Special Issue: 有机氟化学虚拟合辑

ARTICLES

三氟甲磺酸酐介导炔酰胺与吡啶加成反应的研究

宋昊儒^a^,^b, 孙建婷^b, 吕敏^b, 刘艺雯^b^,^*(), 魏邦国^b^,^*()

a 南京大学化学化工学院南京 210046
b 复旦大学药学院上海 200032

收稿日期:2022-03-31 修回日期:2022-04-29 发布日期:2022-05-06
通讯作者: 刘艺雯, 魏邦国
基金资助:
国家自然科学基金(21772027)

Trifluoromethyl Sulfonic Anhydride Mediated Addition of Pyridine with Ynamides

Haoru Song^a^,^b, Jianting Sun^b, Min LÜ^b, Yiwen Liu^b(), Bangguo Wei^b()

a School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, Jiangsu 210046
b School of Pharmacy, Fudan University, Shanghai 200032

Received:2022-03-31 Revised:2022-04-29 Published:2022-05-06
Contact: Yiwen Liu, Bangguo Wei
Supported by:
National Natural Science Foundation of China(21772027)

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Abstract

A convenient approach to pyridine quaternary ammonium salts containing enamine fragment has been developed, which features a trifluoromethyl sulfonic anhydride mediated regioselective addition process of pyridine with ynamides. Using this method, a variety of substituted pyridine quaternary ammonium salts containing enamine fragment 3a~3m were prepared in moderate to excellent yields with high regioselectivities (Z:E up to 20:1).

Key words: ynamides, pyridine, addition reaction, pyridine quaternary ammonium salt

Cite this article

Haoru Song, Jianting Sun, Min LÜ, Yiwen Liu, Bangguo Wei. Trifluoromethyl Sulfonic Anhydride Mediated Addition of Pyridine with Ynamides[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2433-2437.

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Fig. & Tab. 6

Scheme 1. Electrical analysis of three bonds in ynamides

Scheme 2. Addition process of ynamides with pyridine

Entry	Additive (equiv.)	Time/h	Yield^b/%	Z:E^c
1	Sc(OTf)₃ (0.2)	10	NR	—
2	Er(OTf)₃ (0.2)	10	NR	—
3	TfOH (1.1)	1	Complex	—
4	Tf₂O (1.1)	1	85	>20:1
5	Tf₂O (1.1)	2	75	>20:1

Table 1. Screening of optimal conditions for the reaction of ynamides with pyridine

Table 2. Reaction substrate expansion of ynamides with pyridine

Figure 1. Crystal structure of compound 3a

Scheme 3. Speculation on the reaction mechanism of ynamides with pyridine

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三氟甲磺酸酐介导炔酰胺与吡啶加成反应的研究

Trifluoromethyl Sulfonic Anhydride Mediated Addition of Pyridine with Ynamides

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Fig. & Tab. 6

References 15

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