膦催化光促进的烷基碘和苯酚及1,4-二氧六环的以电子转移化合物为媒介的羰基化酯化反应

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

催化学报 ›› 2023, Vol. 48: 214-223.DOI: 10.1016/S1872-2067(23)64398-0

膦催化光促进的烷基碘和苯酚及1,4-二氧六环的以电子转移化合物为媒介的羰基化酯化反应

顾幸威^a^,¹, 张有灿^b^,¹, 赵丰乾^a, 艾汉均^a, 吴小锋^a^,^b^,^*()

^a莱布尼茨催化研究所, 德国
^b中国科学院大连化学物理研究所, 大连洁净能源国家实验室, 辽宁大连116023, 中国

收稿日期:2022-12-21 接受日期:2022-01-23 出版日期:2023-05-18 发布日期:2023-04-20
通讯作者: * 电子信箱: xwu2020@dicp.ac.cn, xiao-feng.wu@catalysis.de (吴小锋).
作者简介:第一联系人：
¹共同第一作者
基金资助:
国家留学基金管理委员会

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

Xing-Wei Gu^a^,¹, Youcan Zhang^b^,¹, Fengqian Zhao^a, Han-Jun Ai^a, Xiao-Feng Wu^a^,^b^,^*()

^aLeibniz-Institut für Katalyse e.V., 18059 Rostock, Germany
^bDalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China

Received:2022-12-21 Accepted:2022-01-23 Online:2023-05-18 Published:2023-04-20
Contact: * E-mail: Xiao-Feng.Wu@catalysis.de, xwu2020@dicp.ac.cn (X.-F. Wu).
About author:First author contact:
¹Contributed equally to this work.
Supported by:
Chinese Scholarship Council

摘要/Abstract

摘要：

在可持续发展化学的框架内, 有机结合电子转移化合物和可见光无疑提供了一条非常理想的选择. 电子转移化合物可以在可见光的照射下被激活, 然后向目标反应进发, 在不需要金属催化剂的情况下实现目标转化. 在各类化合物中, 酯类化合物在各个领域都占据着非常重要的地位. 羰基化酯化反应可以把廉价的一氧化碳分子引入到母体分子中, 如果以醇或者酚作为亲核试剂, 其中酯类化合物可以被直接制得.
本文发展了一种膦催化的光促进烷基碘和苯酚的羰基化酯化反应. 电子转移化合物在可见光照射下得以活化, 在不需要过渡金属催化剂的情况下, 该反应可以在标准大气压的一氧化碳气体氛围下实现. 该反应体系展现出较好的官能团兼容性和较好的化学选择性, 酯基、氟、氯、氰基、酰基、醚、砜等官能团都能够被很好地兼容. 也可以采用天然产物大分子化合物作为原料, 并得到中等收率的目标产物. ¹³碳标记的一氧化碳实验结果表明, 产物中的羰基来源于一氧化碳且能得到中等偏高收率的产物. 机理研究结果验证了反应的自由基属性, 且该反应能够放大到克级. 同时, 利用自由基参与的多米诺反应, 该策略也能被用于多组分的多氟烷基化羰基化反应. 综上, 本文结果也为该策略应用于批量生产及其他领域提供了参考和借鉴.

关键词: 羰基化反应, 电子转移化合物, 酯, 烷基碘, 可见光

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

顾幸威, 张有灿, 赵丰乾, 艾汉均, 吴小锋. 膦催化光促进的烷基碘和苯酚及1,4-二氧六环的以电子转移化合物为媒介的羰基化酯化反应[J]. 催化学报, 2023, 48: 214-223.

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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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(23)64398-0

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

图/表 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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膦催化光促进的烷基碘和苯酚及1,4-二氧六环的以电子转移化合物为媒介的羰基化酯化反应

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

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