Aryl-Iodide-Mediated Electrochemical Aziridination of Electron-Deficient Alkenes

doi:10.6023/cjoc202105046

Abstract

A protocol of electrochemical aziridination of electron-deficient alkenes was reported using phthalhydrazide as nitrogen source. The reaction could be conducted in undivided cell, and the ArI is essential to achieve the transformation. Hypervalent-iodine-stablized nitrene and acetyl hydroxyhydrazine were suggested as the in-situ generated nitrogen source for the stepwise aziridination. This protocol can be applied to the azirdination of α,β-unsaturated esters, amides, nitrile and ketones to give a series N-containing molecules.

Key words: electrochemistry, aziridination, hypervalent iodine, electron-deficient alkene

Cite this article

Feng Liu, Jie Dai, Xu Cheng. Aryl-Iodide-Mediated Electrochemical Aziridination of Electron-Deficient Alkenes[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4014-4020.

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Fig. & Tab. 7

Scheme 1. Reaction design of aziridination of electron-deficient alkene

Entry	Deviation from standard conditions	Yield^b/%
1	None	67
2	ⁿBu₄NCl instead of ⁿBu₄NOAc	33
3	LiOAc instead of ⁿBu₄NOAc	37
4	ⁿBu₄NBF₄ instead of ⁿBu₄NOAc	Trace
5	1, 3, 5, 9 mA instead of 7 mA	35~57
6	EtOH, MeOH, THF, DMSO, DMF as solvent	ND
7	MeCN as solvent	33
8	No 4-MeOC₆H₄I (4)	ND
9	PhI instead of 4	Trace
10	4-FC₆H₄I instead of 4	Trace

Table 1. Optimization of aziridination of cinnamate mediated by ArIa

Scheme 2. Synthetic exploration of electrochemical aziridination reaction

Figure 1. CV analyses of reactants

Table 2. Substrate scope of aziridination of electron-deficient alkenea

Scheme 3. Experiments to investigate the reaction mechanism

Scheme 4. A plausible reaction mechanism for ArI-mediated electrochemical aziridination

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