Phosphine-catalyzed photo-induced alkoxycarbonylation of alkyl iodides with phenols and 1,4-dioxane through charge-transfer complex

doi:10.1016/S1872-2067(23)64398-0

Abstract

Abstract:

The combining of charge-transfer complex and light irradiation offers a promising solution for the requests of sustainable chemistry. Herein, we developed a phosphine-catalyzed visible light-induced alkoxycarbonylation of alkyl iodides with phenols and ethers. Based on the electron donor-acceptor photoactivation strategy, the reaction can be realized at atmospheric pressure of CO under transition metal-free conditions. This promising approach demonstrates high functional group tolerance and excellent chemoselectivity. Additionally, five-component perfluoroalkylative carbonylation for the synthesis of β-perfluoroalkyl acyloxy esters from unactivated olefins and perfluoroalkyl iodides can be realized as well. Moreover, due to the excellent performance of the gram-scale reaction and ¹³CO results, it provides potential opportunities for large-scale production and other applications.

Key words: Carbonylation, Charge-transfer complex, Esters, Alkyl iodide, Visible light

Xing-Wei Gu, Youcan Zhang, Fengqian Zhao, Han-Jun Ai, Xiao-Feng Wu. Phosphine-catalyzed photo-induced alkoxycarbonylation of alkyl iodides with phenols and 1,4-dioxane through charge-transfer complex[J]. Chinese Journal of Catalysis, 2023, 48: 214-223.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(23)64398-0

https://www.cjcatal.com/EN/Y2023/V48/I5/214

Figures/Tables 9

Scheme 1. Strategies for alkyl halide carbonylation.

Table 1 Optimization of the reaction conditions.a

Entry	Variation from the “Standard conditions”	Yield (%)^b
1	none	>96 (95)
2	10 mol% PCy₃	91
3	0.2 mol L^-1 dioxane	95
4^c	ⁿBu₃P instead of PCy₃	90
5^c	PPh₃ instead of PCy₃	n.d.
6^c	(p-FC₆H₄)₃P instead of PCy₃	n.d.
7^c	Na₂CO₃ instead of K₂CO₃	46
8^c	Cs₂CO₃ instead of K₂CO₃	9
9^c	Et₃N instead of K₂CO₃	24
10^c	18 h instead of 24 h	85
11	50 °C instead of 80 °C	68
12	No PCy₃	n.d.
13	No light	n.d.

Scheme 2. Scope of phenols. a Reaction conditions: phenols (0.2 mmol), alkyl iodide (0.3 mmol), K2CO3 (0.3 mmol), PCy3 (20 mol%), 1,4-dioxane (0.5 mL), CO (1 bar), irradiation with blue light (400-500 nm) at 80 °C for 24 h. b PCy3 (50 mol%). c phenols (0.2 mmol), alkyl iodide (0.6 mmol), K2CO3 (0.6 mmol), PCy3 (40 mol%), 1,4-dioxane (1 mL). dThe reaction was performed on a 5 mmol scale (1.27 g).

Scheme 3. Scope of Alkyl iodides. a Reaction conditions: phenols (0.2 mmol), alkyl iodides (0.3 mmol), K2CO3 (0.3 mmol), PCy3 (20 mol%), 1,4-dioxane (0.5 mL), CO (1 bar), irradiation with blue light (400-500 nm) at 80 °C for 24 h. b PCy3 (50 mol%). c (p-FC6H4)3P (30 mol%), 1,4-dioxane (2 mL). dThe reaction was performed on a 0.1 mmol scale. e The reaction was performed under 1 atm of 13CO pressure.

Scheme 4. Mechanistic experiments and proposed mechanism.

Table 2 Optimization of reaction conditions a.

Entry	Variations from the standard conditions	Yield ^b (%)
1	none	56 (53) ^c
2	X-Phos or PCy₃ instead of PPh₃	43, 38
3 ^d	DPPP or Xantphos instead of PPh₃	50, 56
4	adding 3 eq. K₃PO₄	51
5 ^e	K₂CO₃ instead of K₃PO₄	50
6 ^e	Na₃PO₄ instead of K₃PO₄	43
7 ^e	DIPEA instead of K₃PO₄	trace
8	adding 50 uL H₂O	56
9	adding 10 mol% PPh₃	48
10	without PPh₃	31
11	without K₃PO₄	n.d.
12	no light	n.d.

Scheme 5 Substrate scope of alkenes and perfluoroalkyl iodides a-c. a Reaction conditions: alkene (0.2 mmol), alkyl iodide (0.3 mmol), PPh3 (20 mol %), K3PO4 (10 mol %), and H2O (0.1 mL) in 1,4-dioxane (1 mL) at rt for 24 h under CO (40 bar), isolated yield. b ethylene (2 bar), alkyl iodide (0.3 mmol), the isolated yield is calculated based on the perfluorobutyl iodide used. c pentafluoroiodoethane (0.6 mmol).

Scheme 6. Control experiments. (a) Reaction in different solvent; (b) Reactions with alkyl iodide; (c) Reaction with acid.

Scheme 7. Possible mechanism.

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