O2促进下五元环烯胺的C—H亚胺化

doi:10.6023/cjoc202212025

摘要/Abstract

报道了一个O₂促进下五元环烯胺的C—H亚胺化反应. 在微波辐射下, 季酮酸或1,3-环戊二酮衍生的烯胺酮、芳酮醛水合物和芳胺三组分参与的无金属催化反应进展顺利, 以良好的产率和完全的立体选择性得到了一系列α-烯胺基-α-芳酰基亚胺衍生物. 在该反应过程中, 空气充当绿色氧化剂, 水是唯一的副产物.

关键词: 三组分, 区域选择性亚胺化

An O₂-enabled C—H imination of five-membered cyclic enamines is reported. Metal-free catalytic three- component reactions of tetronic acid- or 1,3-cyclopentanedione-derived enaminones with arylglyoxals and arylamines worked well under microwave irradiation, furnishing a series of α-enamino-α-aroyl imines with good yields and complete stereoselectivity. In this reaction process, air serves as the green oxidant with water as the sole byproduct.

Key words: three component, regioselective imination

引用此文

范威. O₂促进下五元环烯胺的C—H亚胺化[J]. 有机化学, 2023, 43(7): 2492-2498.

Wei Fan. O₂-Enabled C—H Imination of Five-Membered Cyclic Enamines[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2492-2498.

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图/表 7

Scheme 1. Methods for the formation of imines

Entry	Solvent	Temp./℃	Yield^b/%
1	EA	100	27
2	EtOH	100	29
3	DCE	100	33
4	Benzene	100	Trace
5	1,4-Dioxane	100	43
6	THF	100	58
7	MeCN	100	68
8	MeCN	110	70
9	MeCN	115	71
10	MeCN	120	73
11	MeCN	125	72
12	MeCN	130	71
13	MeCN	120	73^c
14	MeCN	120	ND^d

Table 1. Optimization for the synthesis of product 4aa

Table 2. Substrate scope for the synthesis of 4a~4h

Table 3. Substrate scope for the synthesis of 4i~4p

Figure 1. ORTEP (Oak Ridge thermal ellipsoid plot) drawing of 4f

Scheme 2. Control reaction

Scheme 3. Mechanism hypothesis for forming 4

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O₂促进下五元环烯胺的C—H亚胺化

O₂-Enabled C—H Imination of Five-Membered Cyclic Enamines

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