Photoredox deoxygenative allylation of carboxylic acids via selective 1,6-addition of acyl radicals to electron-deficient 1,3-dienes

doi:10.1016/S1872-2067(23)64461-4

Chinese Journal of Catalysis ›› 2023, Vol. 50: 215-221.DOI: 10.1016/S1872-2067(23)64461-4

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Photoredox deoxygenative allylation of carboxylic acids via selective 1,6-addition of acyl radicals to electron-deficient 1,3-dienes

Lili Zhang^a, Yuhang Li^a, Zhenyu Guo^a, Yantao Li^a, Nian Li^a, Weipeng Li^a^,^*(), Chengjian Zhu^a^,^b^,^*(), Jin Xie^a^,^*()

^aState Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, Jiangsu, China
^bGreen Catalysis Center, College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, Henan, China

Received:2023-04-14 Accepted:2023-05-08 Online:2023-07-18 Published:2023-07-25
Contact: *E-mail: lwp1989@nju.edu.cn (W. Li), cjzhu@nju.edu.cn (C. Zhu), xie@nju.edu.cn (J. Xie).
Supported by:
National Key Research and Development Program of China(2022YFA1503200);National Key Research and Development Program of China(2021YFC2101901);National Natural Science Foundation of China(22122103);National Natural Science Foundation of China(21971108);National Natural Science Foundation of China(21971111);National Natural Science Foundation of China(22271144);Fundamental Research Funds for the Central Universities(020514380304);Fundamental Research Funds for the Central Universities(020514380252);Fundamental Research Funds for the Central Universities(020514380272);Postgraduate Research & Practice Innovation Program of Jiangsu Province(KYCX22_0100)

Abstract

Abstract:

We report the 1,6-addition of acyl radicals to the electron-deficient 1,3-dienes under visible-light photoredox catalysis. The deoxygenative allylation of the carboxylic acid is achieved under mild conditions, generating the valuable 1,6-dicarbonyl compounds in moderate to good yields (up to 96%). A range of functionalized carboxylic acids are competent coupling partners. This deoxygenative allylation protocol has a high level of regio- and stereo-selectivity as well as good functional group comparability.

Key words: Photoredox catalysis, Acyl radical, 1,3-Dienes, 1,6-Conjugate addition, 1,6-Dicarbonyl compound

Lili Zhang, Yuhang Li, Zhenyu Guo, Yantao Li, Nian Li, Weipeng Li, Chengjian Zhu, Jin Xie. Photoredox deoxygenative allylation of carboxylic acids via selective 1,6-addition of acyl radicals to electron-deficient 1,3-dienes[J]. Chinese Journal of Catalysis, 2023, 50: 215-221.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(23)64461-4

https://www.cjcatal.com/EN/Y2023/V50/I7/215

Figures/Tables 8

Scheme 1. Research progress in functionalization of electron-deficient 1,3-dienes.

Table 1 Optimization of the reaction conditions.

Entry	Additive	Base	Solvent	Yield/%	Conv./%^c
1	Ph₃P	K₂HPO₄	DCM	45^a	48
2	Ph₃P	K₂HPO₄	MeCN	trace	13
3	Ph₃P	K₂HPO₄	DMF	17^a	16
4	Ph₃P	K₂HPO₄	DCM:H₂O (4:1)	53^a	61
5	Ph₂POEt	K₂HPO₄	DCM:H₂O (4:1)	ND	5
6	P(p-Tolyl)₃	K₂HPO₄	DCM:H₂O (4:1)	60^a	71
7	P(p-Anisole)₃	K₂HPO₄	DCM:H₂O (4:1)	78^a (75^b)	84
8	P(p-Anisole)₃	Li₂CO₃	DCM:H₂O (4:1)	71^b	91
9	P(p-Anisole)₃	di-iso-propylamine	DCM:H₂O (4:1)	74^b	82
10	P(p-Anisole)₃	TMP	DCM:H₂O (4:1)	65^b	79
11	P(p-Anisole)₃	di-iso-butylamine	DCM:H₂O (4:1)	83^b	91
12	P(p-Anisole)₃	di-iso-butylamine	DCM:H₂O (9:1)	86^b	93
13^d	P(p-Anisole)₃	di-iso-butylamine	DCM:H₂O (9:1)	39^b	55
14^e	—	di-iso-butylamine	DCM:H₂O (9:1)	ND	0

Scheme 2. Scope of carboxylic acids. E:Z > 95:5 in all cases of 1,6-addition determined by 1H NMR. Reaction conditions: 1 (0.1 mmol), 2a (0.3 mmol), PC-I (2 mol%), P(p-Anisoles)3 (1.2 equiv.), di-iso-butylamine (20 mol%), DCM/H2O (2.0 mL, v/v = 9:1), Ar, rt, 10 W blue LEDs (460 nm), 12 h. a Average yield of three shots.

Scheme 3. Scope of aromatic acids and electron-deficient 1,3-dienes. E:Z > 95:5 in all cases determined by 1H NMR. Reaction conditions: 1 (0.1 mmol), 2 (0.3 mmol), PC-I (2 mol%), P(p-Anisoles)3 (1.2 equiv.), di-iso-butylamine (20 mol%), DCM/H2O (2.0 mL, v/v = 9:1), Ar, rt, 10 W blue LEDs (460 nm), 12 h.

Scheme 4. Gram-scale synthesis of 3aa and control experiments.

Figure 1. The graph of fluorescence quenching of PC-I* by 1a (a), 2a (b) and P(p-Anisole)3 (c), and their Stern-Volmer curves (d).

Figure 2. Cyclic Voltammetry (CV) experiments.

Scheme 5. Proposed mechanism.

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Photoredox deoxygenative allylation of carboxylic acids via selective 1,6-addition of acyl radicals to electron-deficient 1,3-dienes

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