Rhodium-Catalyzed Decarbonylative Suzuki-Miyaura Cross-Coupling via in-Situ Generation of Acyl Fluorides from Carboxylic Acids

doi:10.6023/cjoc202203011

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (7): 2184-2191.DOI: 10.6023/cjoc202203011 Previous Articles Next Articles

Special Issue: 有机氟化学虚拟合辑

ARTICLES

铑催化羧酸原位生成酰氟的脱羰Suzuki-Miyaura偶联

刘晓洁^a^,^b, 徐必平^b^,^*(), 苏伟平^a^,^b^,^*()

^a福州大学化学学院福建福州 350108
^b中国科学院福建物质结构研究所结构化学国家重点实验室福建福州 350002

收稿日期:2022-03-03 修回日期:2022-04-02 发布日期:2022-08-09
通讯作者: 徐必平, 苏伟平
基金资助:
国家重点研发计划(2018FYA0704502); 国家自然科学基金(21931011); 国家自然科学基金(22071241); 中国福建光电信息科学与技术创新实验室(闽都创新实验室)(2021ZZ105)

Rhodium-Catalyzed Decarbonylative Suzuki-Miyaura Cross-Coupling via in-Situ Generation of Acyl Fluorides from Carboxylic Acids

Xiaojie Liu^a^,^b, Biping Xu^b(), Weiping Su^a^,^b()

^aCollege of Chemistry, Fuzhou University, Fuzhou, Fujian 350108
^bState Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002

Received:2022-03-03 Revised:2022-04-02 Published:2022-08-09
Contact: Biping Xu, Weiping Su
Supported by:
National Key Research and Development Program of China(2018FYA0704502); National Natural Science Foundation of China(21931011); National Natural Science Foundation of China(22071241); Fujian Science & Technology Innovation Laboratory for Optoelectronic Information of China(2021ZZ105)

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Abstract

The biaryl frameworks are momentous organic backbones that are commonly occurred in pharmaceutical, functional materials and natural products. By virtue of the distinctive reactivity through state-of-the-art process, decarbonylative couplings, which have bypassed the restriction to specifically substituted (hetero)aryl carboxylic acids of decarboxylative couplings, gradually become unneglected methods in the conversion of carboxylic acid derivatives. Herein, a rhodium-catalyzed decarbonylative Suzuki-Miyaura cross-coupling via in-situ generation strategy of acyl fluorides from carboxylic acids was developed. This protocol shows eminent functional group tolerance with arrays of combinations between carboxylic acid and boronic acid. Furthermore, the reaction offers a new access to those conventionally unattainable biaryl motifs, including natural product and modified drugs.

Key words: rhodium catalysis, decarbonylative cross-coupling, in-situ generation, acyl fluorides

Cite this article

Xiaojie Liu, Biping Xu, Weiping Su. Rhodium-Catalyzed Decarbonylative Suzuki-Miyaura Cross-Coupling via in-Situ Generation of Acyl Fluorides from Carboxylic Acids[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2184-2191.

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Entry	Catalyst (5 mol%)	Ligand	Yield^b/%
1	Rh(PPh)₃Cl	—	32
2	[Rh(OAc)₂]₂	—	Trace
3	[Rh(C₂H₄)₂Cl]₂	—	7
4	[Rh(COD)Cl]₂	—	39
5	[Rh(COD)Cl]₂	IMes•HCl (20 mol%)	11
6	[Rh(COD)Cl]₂	IPr•HCl (20 mol%)	9
7	[Rh(COD)Cl]₂	DPPM (10 mol%)	13
8	[Rh(COD)Cl]₂	DPPE (10 mol%)	26
9	[Rh(COD)Cl]₂	DPPF (10 mol%)	7
10	[Rh(COD)Cl]₂	PPh₃ (20 mol%)	42
11	[Rh(COD)Cl]₂	P(2-furyl)₃ (20 mol%)	21
12	[Rh(COD)Cl]₂	P(4-MeOC₆H₅)₃ (20 mol%)	11
13	[Rh(COD)Cl]₂	P(4-CF₃C₆H₅)₃ (20 mol%)	51
14	[Rh(COD)Cl]₂	P(C₆F₅)₃ (20 mol%)	87 (81)
15^c	[Rh(COD)Cl]₂	P(C₆F₅)₃ (20 mol%)	51
16^d	[Rh(COD)Cl]₂	P(C₆F₅)₃ (20 mol%)	67
17^e	[Rh(COD)Cl]₂	P(C₆F₅)₃ (20 mol%)	84
18^f	[Rh(COD)Cl]₂	P(C₆F₅)₃ (20 mol%)	53

Entry	Catalyst (5 mol%)	Ligand	Yield^b/%
1	Rh(PPh)₃Cl	—	32
2	[Rh(OAc)₂]₂	—	Trace
3	[Rh(C₂H₄)₂Cl]₂	—	7
4	[Rh(COD)Cl]₂	—	39
5	[Rh(COD)Cl]₂	IMes•HCl (20 mol%)	11
6	[Rh(COD)Cl]₂	IPr•HCl (20 mol%)	9
7	[Rh(COD)Cl]₂	DPPM (10 mol%)	13
8	[Rh(COD)Cl]₂	DPPE (10 mol%)	26
9	[Rh(COD)Cl]₂	DPPF (10 mol%)	7
10	[Rh(COD)Cl]₂	PPh₃ (20 mol%)	42
11	[Rh(COD)Cl]₂	P(2-furyl)₃ (20 mol%)	21
12	[Rh(COD)Cl]₂	P(4-MeOC₆H₅)₃ (20 mol%)	11
13	[Rh(COD)Cl]₂	P(4-CF₃C₆H₅)₃ (20 mol%)	51
14	[Rh(COD)Cl]₂	P(C₆F₅)₃ (20 mol%)	87 (81)
15^c	[Rh(COD)Cl]₂	P(C₆F₅)₃ (20 mol%)	51
16^d	[Rh(COD)Cl]₂	P(C₆F₅)₃ (20 mol%)	67
17^e	[Rh(COD)Cl]₂	P(C₆F₅)₃ (20 mol%)	84
18^f	[Rh(COD)Cl]₂	P(C₆F₅)₃ (20 mol%)	53

铑催化羧酸原位生成酰氟的脱羰Suzuki-Miyaura偶联

Rhodium-Catalyzed Decarbonylative Suzuki-Miyaura Cross-Coupling via in-Situ Generation of Acyl Fluorides from Carboxylic Acids

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