Iridium-Catalyzed Intermolecular N—N Coupling for Hydrazide Synthesis Using N-Benzoyloxycarbamates as Acyl Nitrene Precursor

doi:10.6023/cjoc202105044

Abstract

An iridium-catalyzed intermolecular N—N coupling reaction using various N-benzoyloxyamides as acyl nitrene precursor for hydrazide synthesis has been developed. Unlike the carboxylic acid-derived dioxazolones used in previous report, this type of precursors allows the efficient synthesis of both acyl and oxycarbonyl substituted hydrazines from readily accessible precursors. Computational chemistry studies indicated that formation of the metal-acylnitrenoid intermediates via intramolecular hydrogen bond-assisted N—O cleavage may be the rate-determining step, and the subsequent nucleophilic attack of metal-acylnitrenoid by arylamines may be assisted by Cl…HN hydrogen bond to form the N—N bond.

Key words: iridium catalysis, nitrene, N—N coupling, hydrazide, N—H insertion

Cite this article

Fangfang Song, Shiyang Zhu, Hao Wang, Gong Chen. Iridium-Catalyzed Intermolecular N—N Coupling for Hydrazide Synthesis Using N-Benzoyloxycarbamates as Acyl Nitrene Precursor[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4050-4058.

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Entry	Variation from the standard conditions	Yield^a/%
1	Standard condition	97 (94)^b
2	No [Cp*IrCl₂]₂	No reaction
3	Solvent free	92
4	[1]=0.1 mol/L	95
5	1.2 equiv. 2e was added	82
6	HFIP as solvent	No reaction
7	DCE as solvent	93
8	Ar atmosphere	92
9	FeCl₂•4H₂O (5 mol%) as catalyst	No reaction
10	T=60 ℃	77
11	AgSbF₆ (5 mol%)	15

Entry	Variation from the standard conditions	Yield^a/%
1	Standard condition	97 (94)^b
2	No [Cp*IrCl₂]₂	No reaction
3	Solvent free	92
4	[1]=0.1 mol/L	95
5	1.2 equiv. 2e was added	82
6	HFIP as solvent	No reaction
7	DCE as solvent	93
8	Ar atmosphere	92
9	FeCl₂•4H₂O (5 mol%) as catalyst	No reaction
10	T=60 ℃	77
11	AgSbF₆ (5 mol%)	15

铱催化异羟肟酸衍生物参与的分子间N—N键偶联反应合成酰肼