Boryl Radical-Promoted Synthesis of Biaryls and Benzylcarboxylic Acids Methyl Ester via C—C Bond Formation Reactions

doi:10.6023/cjoc202402012

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (6): 1853-1861.DOI: 10.6023/cjoc202402012 Previous Articles Next Articles

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硼自由基促进的C—C键形成反应构筑联芳基和苄基羧酸甲酯

李文多^a^,^*(), 魏娜娜^b, 冯楠^c

a 陇东学院石油化工学院甘肃省陇东油气资源高效利用重点实验室甘肃庆阳 745000
b 陇东学院生命科学与技术学院甘肃省陇东生物资源保护利用与生态修复重点实验室甘肃庆阳 745000
c 陇东学院石油化工学院甘肃庆阳 745000

收稿日期:2024-02-22 修回日期:2024-03-24 发布日期:2024-05-10
基金资助:
甘肃省自然科学基金(22JR5RM203); 陇东学院博士基金(XYBYZK2221); 陇东学院博士基金(XYBYZK2224); 陇东学院青年科技创新基金(XYZK2303); 甘肃省教育厅创新基金(2024A-164)

Boryl Radical-Promoted Synthesis of Biaryls and Benzylcarboxylic Acids Methyl Ester via C—C Bond Formation Reactions

Wenduo Li^a,*(), Na'na Wei^b, Nan Feng^c

a Gansu Key Laboratory of Efficient Utilization of Oil and Gas Resources in Longdong, College of Petroleum and Chemical Engineering, Longdong University, Qingyang, Gansu 745000
b Gansu Key Laboratory of Conservation and Utilization of Biological Resources and Ecological Restoration in Longdong, College of Life Science & Technology, Longdong University, Qingyang, Gansu 745000
c College of Petroleum and Chemical Engineering, Longdong University, Qingyang, Gansu 745000

Received:2024-02-22 Revised:2024-03-24 Published:2024-05-10
Contact: * E-mail: lwd0522@126.com
Supported by:
Natural Science Foundation of Gansu Province(22JR5RM203); Doctor Foundation of Longdong University(XYBYZK2221); Doctor Foundation of Longdong University(XYBYZK2224); Youth Scientific and Technical Innovation Foundation of Longdong University(XYZK2303); Innovation Fund Project of Gansu Education Department(2024A-164)

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Abstract

A facile route for the formation of C—C bonds with tetraarylborates as boryl radical precursors under organophotoredox conditions is developed. This strategy has been verified to be applicable not only for the preparation of symmetrical and unsymmetrical biaryls, but also for direct carboxylation of a range of free benzyl alcohols. Control experiments and mechanism studies indicated that aryl boron radical species is a reactive intermediate.

Key words: photoredox catalysis, tetraarylborate, boryl radical, formation of C—C bond, biaryl compound, carboxylic acid

Cite this article

Wenduo Li, Na'na Wei, Nan Feng. Boryl Radical-Promoted Synthesis of Biaryls and Benzylcarboxylic Acids Methyl Ester via C—C Bond Formation Reactions[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1853-1861.

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Fig. & Tab. 7

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Entry	Variations from “standard conditions”'	Yield^b/% of 2a
1	None	93 (91)^c
2	Ir[dF(CF₃)ppy]₂(dtbbpy)PF₆ instead of 4-CzIPN	92
3	N₂ instead of O₂	63
4	Open to air instead of under O₂	78
5	Under N₂ and with degassed CH₃CN	26
6	DMF instead of CH₃CN	90
7	1,4-Dioxane instead of CH₃CN	70
8	DCM instead of CH₃CN	43
9	B-1 instead of NaBPh₄	89
10	B-2 instead of NaBPh₄	84
11	B-3 instead of NaBPh₄	93
12	B-4 instead of NaBPh₄	92
13	B-5 instead of NaBPh₄	88
14	Without photocatalyst	0
15	Without blue LEDs	0

Entry	Variations from “standard conditions”'	Yield^b/% of 2a
1	None	93 (91)^c
2	Ir[dF(CF₃)ppy]₂(dtbbpy)PF₆ instead of 4-CzIPN	92
3	N₂ instead of O₂	63
4	Open to air instead of under O₂	78
5	Under N₂ and with degassed CH₃CN	26
6	DMF instead of CH₃CN	90
7	1,4-Dioxane instead of CH₃CN	70
8	DCM instead of CH₃CN	43
9	B-1 instead of NaBPh₄	89
10	B-2 instead of NaBPh₄	84
11	B-3 instead of NaBPh₄	93
12	B-4 instead of NaBPh₄	92
13	B-5 instead of NaBPh₄	88
14	Without photocatalyst	0
15	Without blue LEDs	0

Entry	Tetraarylborate	Biaryl	Entry	Tetraarylborate	Biaryl
1			5
2			6
3			7
4			8

Entry	Tetraarylborate	Biaryl	Entry	Tetraarylborate	Biaryl
1			5
2			6
3			7
4			8

硼自由基促进的C—C键形成反应构筑联芳基和苄基羧酸甲酯

Boryl Radical-Promoted Synthesis of Biaryls and Benzylcarboxylic Acids Methyl Ester via C—C Bond Formation Reactions

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