Phosphine-Catalyzed Synthesis of 1,3-Dihydro-3-alkylidene-2H-indol-2-ones

doi:10.6023/cjoc202201030

Abstract

A P(4-OMe-C₆H₄)₃-catalyzed Michael addition/double bond migration tandem reaction between allenyl imide and indol-2-ones was developed. This synthetic strategy for diverse 1,3-dihydro-3-alkylidene-2H-indol-2-ones features operationally simple, good substrate scope, high chemoselectivity and mild reaction conditions. The proposed reaction mechanism is also provided.

Key words: indol-2-one, allene, phosphine catalysis, Michael addition, double bond migration

Cite this article

Jingjie Li, Yuhao Wang, Tiantian Meng, Yiyong Huang. Phosphine-Catalyzed Synthesis of 1,3-Dihydro-3-alkylidene-2H-indol-2-ones[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2222-2228.

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Entry	Catalyst	Solvent	Time/h	Yield^b/%
Entry	Catalyst	Solvent	Time/h	3a	4a
1	PBu₃	EtOAc	48	34^c	34^c
2	PBu₃	Et₂O	48	49	—
3	P(4-MeOC₆H₄)₃	Et₂O	18	62	—
4	P(4-MeOC₆H₄)₃	THF	48	38	39
5	P(4-MeOC₆H₄)₃	DCE	48	42	36
6	P(4-MeOC₆H₄)₃	MTBE	48	10	35
7	P(4-MeOC₆H₄)₃	CH₃CN	48	50	—
8	P(4-MeOC₆H₄)₃	CH₃OH	48	—	—
9	P(4-MeOC₆H₄)₃	DMF	48	72	—
10	P(4-MeOC₆H₄)₃	DMF	24	81^d	—

Entry	Catalyst	Solvent	Time/h	Yield^b/%
Entry	Catalyst	Solvent	Time/h	3a	4a
1	PBu₃	EtOAc	48	34^c	34^c
2	PBu₃	Et₂O	48	49	—
3	P(4-MeOC₆H₄)₃	Et₂O	18	62	—
4	P(4-MeOC₆H₄)₃	THF	48	38	39
5	P(4-MeOC₆H₄)₃	DCE	48	42	36
6	P(4-MeOC₆H₄)₃	MTBE	48	10	35
7	P(4-MeOC₆H₄)₃	CH₃CN	48	50	—
8	P(4-MeOC₆H₄)₃	CH₃OH	48	—	—
9	P(4-MeOC₆H₄)₃	DMF	48	72	—
10	P(4-MeOC₆H₄)₃	DMF	24	81^d	—

1,3-二氢-3-亚烷基-吲哚-2-酮的膦催化合成研究