蓝光诱导的1,3-二酮C(CO)—C键卡宾插入反应

doi:10.6023/cjoc202201045

摘要/Abstract

可见光诱导被认为是绿色化学合成中的理想“工具”. 可见光诱导的反应具有条件温和、设备简单及副产物少等优点, 逐渐发展成为有机合成领域重要的方法之一. 报道了蓝光诱导溴化锂促进的重氮酸酯卡宾插入1,3-二酮底物C(CO)—C键的反应, 合成了一系列含全碳季碳中心的1,4-二酮化合物. 该合成方法具有良好的底物普适性和官能团兼容性, 是一种理想高效的1,4-二酮化合物合成策略.

关键词: 蓝光, 路易斯酸, 卡宾, 1, 3-二酮, 碳碳键断裂

Visible light is an ideal “tool” for the green chemical synthesis. Visible light-induced reactions show such advantages as mild reaction conditions, simple equipments and less by-products. Therefore, it has gradually become an important method in organic synthesis. Herein an blue light induced LiBr-promoted carbene insertion reaction of diazoesters into C(CO)—C bonds of 1,3-diones for the synthesis of a wide range of all-carbon quaternary center-containing 1,4-dione derivatives is reported. The method features good substrate universality and functional group compatibility, and therefore is an ideal and efficient strategy for the synthesis of 1,4-diones.

Key words: blue light, Lewis acid, carbene, 1, 3-dione, carbon-carbon bond cleavage

引用此文

巴聃, 程国林. 蓝光诱导的1,3-二酮C(CO)—C键卡宾插入反应[J]. 有机化学, 2022, 42(9): 2888-2897.

Dan Ba, Guolin Cheng. Blue Light Induced Insertion of Carbene into C(CO)—C Bonds of 1,3-Diones[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2888-2897.

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参考文献 16

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Entry	Additive	Solvent	Light source	Yield^b/%
1	—	DCM	Blue LEDs	45
2	—	DCE	Blue LEDs	33
3	—	CHCl₃	Blue LEDs	37
4	—	DMSO	Blue LEDs	0
5	—	MeCN	Blue LEDs	23
6	—	EA	Blue LEDs	30
7	—	Toluene	Blue LEDs	41
8	—	THF	Blue LEDs	0
9	—	MeOH	Blue LEDs	Trace
10	—	DMF	Blue LEDs	0
11	Pyridine	DCM	Blue LEDs	Trace
12	DBU	DCM	Blue LEDs	34
13	Et₃N	DCM	Blue LEDs	35
14	CsF	DCM	Blue LEDs	Trace
15	^tBuONa	DCM	Blue LEDs	Trace
16	Na₂CO₃	DCM	Blue LEDs	38
17	KI	DCM	Blue LEDs	47
18	K₂CO₃	DCM	Blue LEDs	26
19	KBr	DCM	Blue LEDs	49
20	LiBr	DCM	Blue LEDs	51
21	LiOH	DCM	Blue LEDs	Trace
22	LiCl	DCM	Blue LEDs	43
23	LiF	DCM	Blue LEDs	46
24	LiBr	DCM	Green LEDs	0
25	LiBr	DCM	Orange LEDs	0
26	LiBr	DCM	UV LEDs	Trace
27	LiBr	DCM	White LEDs	40
28	LiBr	DCM	Dark	0
29^c	LiBr	DCM	Blue LEDs	51
30^d	LiBr	DCM	Blue LEDs	49
31^e	LiBr	DCM	Blue LEDs	75
32^f	LiBr	DCM	Blue LEDs	60
33^g	LiBr	DCM	Blue LEDs	83
34^h	LiBr	DCM	Blue LEDs	81

Entry	Additive	Solvent	Light source	Yield^b/%
1	—	DCM	Blue LEDs	45
2	—	DCE	Blue LEDs	33
3	—	CHCl₃	Blue LEDs	37
4	—	DMSO	Blue LEDs	0
5	—	MeCN	Blue LEDs	23
6	—	EA	Blue LEDs	30
7	—	Toluene	Blue LEDs	41
8	—	THF	Blue LEDs	0
9	—	MeOH	Blue LEDs	Trace
10	—	DMF	Blue LEDs	0
11	Pyridine	DCM	Blue LEDs	Trace
12	DBU	DCM	Blue LEDs	34
13	Et₃N	DCM	Blue LEDs	35
14	CsF	DCM	Blue LEDs	Trace
15	^tBuONa	DCM	Blue LEDs	Trace
16	Na₂CO₃	DCM	Blue LEDs	38
17	KI	DCM	Blue LEDs	47
18	K₂CO₃	DCM	Blue LEDs	26
19	KBr	DCM	Blue LEDs	49
20	LiBr	DCM	Blue LEDs	51
21	LiOH	DCM	Blue LEDs	Trace
22	LiCl	DCM	Blue LEDs	43
23	LiF	DCM	Blue LEDs	46
24	LiBr	DCM	Green LEDs	0
25	LiBr	DCM	Orange LEDs	0
26	LiBr	DCM	UV LEDs	Trace
27	LiBr	DCM	White LEDs	40
28	LiBr	DCM	Dark	0
29^c	LiBr	DCM	Blue LEDs	51
30^d	LiBr	DCM	Blue LEDs	49
31^e	LiBr	DCM	Blue LEDs	75
32^f	LiBr	DCM	Blue LEDs	60
33^g	LiBr	DCM	Blue LEDs	83
34^h	LiBr	DCM	Blue LEDs	81