Iron phthalocyanine-catalyzed radical phosphinoylazidation of alkenes: A facile synthesis of β-azido-phosphine oxide with a fast azido transfer step

doi:10.1016/S1872-2067(21)63847-0

Abstract

Abstract:

Phosphinoylazidation of alkenes is a direct method to build nitrogen- and phosphorus-containing compounds from feed-stock chemicals. Notwithstanding the advances in other phosphinyl radical related difunctionalization of alkenes, catalytic phosphinoylazidation of alkenes has not yet been reported. Here, we describe the first iron-catalyzed intermolecular phosphinoylazidation of styrenes and unactivated alkenes. The method is practically useful and requires a relatively low loading of catalyst. Mechanistic studies confirmed the radical nature of the reaction and disclosed the unusually low activation energy 4.8 kcal/mol of radical azido group transfer from the azidyl iron(III) phthalocyanine species (PcFeIIIN3) to a benzylic radical. This work may help to clarify the mechanism of iron-catalyzed azidation, inspire other mechanism studies and spur further synthetic applications.

Key words: Iron phthalocyanine, Phosphinoylazidation, Difunctionalization, Radical group transfer, Density functional theory calculation

Xiaoxu Ma, Mong-Feng Chiou, Liang Ge, Xiaoyan Li, Yajun Li, Li Wu, Hongli Bao. Iron phthalocyanine-catalyzed radical phosphinoylazidation of alkenes: A facile synthesis of β-azido-phosphine oxide with a fast azido transfer step[J]. Chinese Journal of Catalysis, 2021, 42(10): 1634-1640.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(21)63847-0

https://www.cjcatal.com/EN/Y2021/V42/I10/1634

Figures/Tables 10

Fig. 1. Biologically important nitrogen-containing phosphonates and the phosphinoylazidation of alkenes.

Fig. 2. Metal-involved radical azido group transfer.

Table 1 Optimization of the reaction conditions. a

Entry	Variation from “standard conditions”	Yield (%)^b
1	Standard reaction conditions ^a	84
2 ^c	Fe(OTf)₂ instead of PcFe	27 ^d
3 ^c	AgNO₃ instead of PcFe	trace ^d
4^c	AgOTf instead of PcFe	trace ^d
5^c	Mn(OAc)₂·4H₂O instead of PcFe	trace ^d
6	40 ^oC instead of rt	43
7	70 ^oC instead of rt	11
8	THF instead of CH₃CN	17
9	PhCl instead of CH₃CN	56
10	1,4-Dioxane instead of CH₃CN	49
11	LPO instead of TBHP	78
12	NFSI instead of TBHP	0
13 ^e	5 mmol reaction	87

Fig. 3. Substrate scope of alkenes. a,b

Fig. 4. Substrate scope of phosphorous substrates. a,b

Fig. 5. Further transformations of products.

Fig. 6. Radical clock and radical trapping experiments.

Fig. 7. The free energy profile for the formation of iron-azide species from 3PcFe.

Fig. 8. Transition states of azide transfer refer to through internal and terminal nitrogen, Ni and Nt, on triplet and quintet surfaces. Spin density isosurfaces of 3TS3-Ni and 5TS3-Nt are displayed.

Fig. 9. Proposed PcFe-catalyzed phosphinoylazidation mechanism.

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