有机硒催化肟转化为腈或酮

doi:10.6023/cjoc202109036

摘要/Abstract

1-氟吡啶三氟甲烷磺酸盐(FP-OTf)和二苯基二硒醚在空气中反应生成苯次硒酸和苯亚硒酸, 这种混合物可以催化醛肟和酮肟分别转化腈或酮. 通过改变二苯基二硒醚的用量及其与FP-OTf的物质的量之比, 能够提高以上两类反应的催化效果. 当二苯基二硒醚用量为5 mol%, FP-OTf的用量为4 mol%时, 可以催化醛肟以较高的产率转化为腈(57%~94%), 而在酮肟转化为酮的反应中, 二苯基二硒醚的用量为2.5 mol%, 且与FP-OTf的物质的量之比为1∶1.2时, 产率较高(74%~91%).

关键词: 肟, 腈, 酮, 二苯基二硒醚, 1-氟吡啶三氟甲烷磺酸盐, 催化

Phenylselenenic acid and phenylseleninic acid were formed in situ in the reaction of diphenyl diselenide with 1-fluoropyridine trifluoromethane sulfonate (FP-OTf) in air. This mixture can catalyze the conversion of aldoxime to nitrile or ketoxime to ketone, respectively. The catalytic effect on those two kinds of reactions can be improved by changing the amount of diphenyl diselenide and the ratio of diphenyl diselenide to FP-OTf. Nitriles were obtained from the open-air reaction of aldoxime catalyzed by the mixture of diphenyl diselenide (5 mol%) and FP-OTf (4 mol%) with the yields of 57%~94%. In the conversion of ketoximes to ketones, higher yields of ketones (74%~91%) were obtaied when the ratio of diphenyl diselenide to FP-OTf was 1∶1.2 and the dosage of diphenyl diselenide was 2.5 mol%.

Key words: oxime, nitrile, ketone, diphenyl diselenide, 1-fluoropyridine trifluoromethane sulfonate, catalysis

引用此文

王利敏, 李柯, 张万轩. 有机硒催化肟转化为腈或酮[J]. 有机化学, 2022, 42(4): 1235-1240.

Liming Wang, Ke Li, Wanxuan Zhang. Organoselenium-Catalyzed Conversion of Oximes to Nitriles or Ketones[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1235-1240.

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Entry	Oxime 1/2	Product 3/4	Yield/%
1^a	1a R¹=Ph, R²=H	3a R¹=Ph	94
2^a	1b R¹=4-Et-C₆H₄, R²=H	3b R¹=4-Et-C₆H₄	76
3^a	1c R¹=4-HOC₆H₄, R²=H	3c R¹=4-HOC₆H₄	88
4^a	1d R¹=4-NCC₆H₄, R²=H	3d R¹=4-NCC₆H₄	57
5^a	1e R¹=4-ClC₆H₄, R²=H	3e R¹=4-ClC₆H₄	67
6^a	1f R¹=3-MeC₆H₄, R²=H	3f R¹=3-Me-C₆H₄	75
7^a	1g R¹=PhCH₂CH₂, R²=H	3g R¹=PhCH₂CH₂	84
8^a	1h R¹=4-i-PrC₆H₄CH₂CHCH₃, R²=H	3h R¹=4-i-PrC₆H₄CH₂CHCH₃	80
9^b^,^c	2a R¹=Ph, R²=CH₃	4a R¹=Ph, R²=CH₃	88
10^b^,^c	2bR¹=4-NO₂C₆H₄, R²=CH₃	4b R¹=4-NO₂C₆H₄, R²=CH₃	74
11^b^,^c	2c R¹=4-MeC₆H₄, R²=CH₃	4c R¹=4-MeC₆H₄, R²=CH₃	85
12^b^,^d	2d R¹=4-ClC₆H₄, R²=CH₃	4d R¹=4-ClC₆H₄, R²=CH₃	90
13^b^,^d	2e R¹=4-CH₃OC₆H₄, R²=CH₃	4e R¹=4-CH₃OC₆H₄, R²=CH₃	75
14^b^,^e	2f R¹=Ph, R²=Ph	4f R¹=Ph, R²=Ph	91
15^b^,^d	2g	4g	78

Entry	Oxime 1/2	Product 3/4	Yield/%
1^a	1a R¹=Ph, R²=H	3a R¹=Ph	94
2^a	1b R¹=4-Et-C₆H₄, R²=H	3b R¹=4-Et-C₆H₄	76
3^a	1c R¹=4-HOC₆H₄, R²=H	3c R¹=4-HOC₆H₄	88
4^a	1d R¹=4-NCC₆H₄, R²=H	3d R¹=4-NCC₆H₄	57
5^a	1e R¹=4-ClC₆H₄, R²=H	3e R¹=4-ClC₆H₄	67
6^a	1f R¹=3-MeC₆H₄, R²=H	3f R¹=3-Me-C₆H₄	75
7^a	1g R¹=PhCH₂CH₂, R²=H	3g R¹=PhCH₂CH₂	84
8^a	1h R¹=4-i-PrC₆H₄CH₂CHCH₃, R²=H	3h R¹=4-i-PrC₆H₄CH₂CHCH₃	80
9^b^,^c	2a R¹=Ph, R²=CH₃	4a R¹=Ph, R²=CH₃	88
10^b^,^c	2bR¹=4-NO₂C₆H₄, R²=CH₃	4b R¹=4-NO₂C₆H₄, R²=CH₃	74
11^b^,^c	2c R¹=4-MeC₆H₄, R²=CH₃	4c R¹=4-MeC₆H₄, R²=CH₃	85
12^b^,^d	2d R¹=4-ClC₆H₄, R²=CH₃	4d R¹=4-ClC₆H₄, R²=CH₃	90
13^b^,^d	2e R¹=4-CH₃OC₆H₄, R²=CH₃	4e R¹=4-CH₃OC₆H₄, R²=CH₃	75
14^b^,^e	2f R¹=Ph, R²=Ph	4f R¹=Ph, R²=Ph	91
15^b^,^d	2g	4g	78