Visible-Light-Induced Annulative Acylative Difunctionalization of 1,6-Enynes for Accessing 1-Indanones

doi:10.6023/cjoc202407040

Abstract

A new photocatalytic annulative acylative difunctionalization of 1,6-enynes is reported, enabling stereoselective access to acylated 1-indanones with cyclic quaternary centers in moderate to good yields. This photocatalysis enables two types of acylation of unsaturated hydrocarbons by adjusting the categories of acyl radical precursors. Aroyl chlorides as bifunctional reagents react with 1,6-enynes to realize annulative chloroacylation, while acyl oxime esters are used as acyl radical precursors, which undergo a three-component annulative alkoxyacylation by treatment with 1,6-enynes and alcohols. The current method demonstrates good functional group compatibility, a broad substrate scope and mild reaction conditions

Key words: photoredox catalysis, annulative chloroacylation, annulative alkoxyacylation, 1,6-enynes

Cite this article

Feng Lin, Yan Zhang, Ming Wu, Huiyan Liu, Wen-Juan Hao, Bo Jiang. Visible-Light-Induced Annulative Acylative Difunctionalization of 1,6-Enynes for Accessing 1-Indanones[J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1729-1738.

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Entry	Variation of the established conditions	Yield^b/%
1	None	85
2	1.0 mol% fac-Ir(ppy)₃	77
3	5.0 mol% fac-Ir(ppy)₃	85
4	2,4,6-Collidine (20 mol%) as the base	30
5	2,6-Lutidine (20 mol%) as the base	45
6	DMAP (20 mol%) as the base	0
7	2,6-Dichloropyridine (10 mol%)	56
8	THF instead of EtOAc	NR
9	In the air	Trace
10	Ru(bpy)₃Cl₂•6H₂O instead of fac-Ir(ppy)₃	Trace
11	Without fac-Ir(ppy)₃	0
12	No light	0

Entry	Variation of the established conditions	Yield^b/%
1	None	85
2	1.0 mol% fac-Ir(ppy)₃	77
3	5.0 mol% fac-Ir(ppy)₃	85
4	2,4,6-Collidine (20 mol%) as the base	30
5	2,6-Lutidine (20 mol%) as the base	45
6	DMAP (20 mol%) as the base	0
7	2,6-Dichloropyridine (10 mol%)	56
8	THF instead of EtOAc	NR
9	In the air	Trace
10	Ru(bpy)₃Cl₂•6H₂O instead of fac-Ir(ppy)₃	Trace
11	Without fac-Ir(ppy)₃	0
12	No light	0

Entry	Variation of the established conditions	Yield^b/%
1	None	45
2	1.0 mol% of fac-Ir(ppy)₃	45
3	1.0 mol% of fac-Ir(ppy)₃ without base	65
4	EtOH instead of MeOH	Trace
5	K₂CO₃ (2.0 equiv.)	21
6	Na₂CO₃ (2.0 equiv.)	53
7	Eosin Y instead of fac-Ir(ppy)₃	32
8	Ru(bpy)₃Cl₂•6H₂O instead of fac-Ir(ppy)₃	Trace
9	In the air	55
10	Without fac-Ir(ppy)₃	0
11	No light	0

Entry	Variation of the established conditions	Yield^b/%
1	None	45
2	1.0 mol% of fac-Ir(ppy)₃	45
3	1.0 mol% of fac-Ir(ppy)₃ without base	65
4	EtOH instead of MeOH	Trace
5	K₂CO₃ (2.0 equiv.)	21
6	Na₂CO₃ (2.0 equiv.)	53
7	Eosin Y instead of fac-Ir(ppy)₃	32
8	Ru(bpy)₃Cl₂•6H₂O instead of fac-Ir(ppy)₃	Trace
9	In the air	55
10	Without fac-Ir(ppy)₃	0
11	No light	0

利用可见光引发1,6-烯炔的增环酰化双官能化制备1-茚酮衍生物