CuI-Catalyzed C—C Bond Coupling Reaction for the Construction of 2-Carbonyl-1,4-diketones

doi:10.6023/cjoc202506032

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (2): 603-611.DOI: 10.6023/cjoc202506032 Previous Articles Next Articles

ARTICLES

CuI催化C—C键偶联反应构建2-羰基-1,4-二酮

刘颖杰^a, 闵来生^a, 杨锐蓉^b, 宋冬雪^a, 彭瑞^a, 梁德强^b^,^*()

^a 哈尔滨商业大学药物工程技术研究中心哈尔滨 150076
^b 昆明学院化学化工学院昆明 650214

收稿日期:2025-06-16 修回日期:2025-09-12 发布日期:2025-10-09
通讯作者: 梁德强
基金资助:
黑龙江省省属本科高校优秀青年教师基础研究支持计划(YQJH2024096); 黑龙江省自然联合引导培育(PL2024H198)

CuI-Catalyzed C—C Bond Coupling Reaction for the Construction of 2-Carbonyl-1,4-diketones

Yingjie Liu^a, Laisheng Min^a, Ruirong Yang^b, Dongxue Song^a, Rui Peng^a, Deqiang Liang^b^,^*()

^a Engineering Research Center for Medicine, Harbin University of Commerce, Harbin 150076
^b School of Chemistry and Chemical Engineering, Kunming University, Kunming 650214

Received:2025-06-16 Revised:2025-09-12 Published:2025-10-09
Contact: Deqiang Liang
Supported by:
Basic Research Support Program for Outstanding Young Teachers in Provincial Undergraduate Colleges and Universities in Heilongjiang Province(YQJH2024096); Heilongjiang Province Natural Joint Guidance Cultivation Project(PL2024H198)

1. .pdf(7206KB)

Abstract

Transition metal-catalyzed C—C coupling reactions are a core strategy for the construction of carbon-carbon bonds in organic synthesis. Their development has not only promoted the synthesis of drugs, materials, and natural products, but also promoted the development of new synthetic methods, and has also made breakthroughs in mechanism innovation and catalyst design. On this basis, a copper-catalyzed radical reaction between ketones is reported, enabling the synthesis of 2-carbonyl-1,4- diones. The method exhibits excellent applicability to multiple structural types of ketones, including aliphatic ketones with diverse substituents, aromatic ketones, and various simple ketones not limited to acetone, with wide applications, easy implementation, low catalyst toxicity, and low cost, cost-effective, and the product is easy to separate and purify.

Key words: transition metal catalysis, C—C coupling, radical reaction, 2-carbonyl-1,4-dione

Cite this article

Yingjie Liu, Laisheng Min, Ruirong Yang, Dongxue Song, Rui Peng, Deqiang Liang. CuI-Catalyzed C—C Bond Coupling Reaction for the Construction of 2-Carbonyl-1,4-diketones[J]. Chinese Journal of Organic Chemistry, 2026, 46(2): 603-611.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 3

References 24

[1]	a) Kumar S.; Jyoti J.; Gupta D. SynOpen 2023, 7, 580.
	(b) Perez Sestelo J.; Sarandeses L. A. Molecules 2020, 25, 4500.
	(c) Song F.; Wang B.; Shi Z. J. Acc. Chem. Res. 2023, 56, 2867.
	(d) Wickham L. M.; Giri R. Acc. Chem. Res. 2021, 54, 3415.
	(e) Duan A.; Xiao F.; Lan Y.; Wang C.; Liu. L.; Zhang Z. Chem. Soc. Rev. 2022, 51, 9986.
[2]	a) Yorimitsu H.; Kotora M.; Patil, N T. Chem. Rec. 2021, 21, 3335.
	(b) Docherty J. H.; Lister T. M.; Mcarthur G.; Findlay J. R.; Kerr W. J.; Andersson H. M.; Donohoe T. J. Chem. Rev. 2023, 123, 7692.
	(c) Bag D, Mahajan S, Sawant, S D. Adv. Synth. Catal. 2020, 362, 3948.
[3]	a) Gramage-Doria R.; Bruneau C. Synthesis 2023, 55, 3470.
	(b) Lee H. E.; Kim D.; You A.; Kim S.; Lee P. H. Catalysts 2020, 10, 861.
	(c) Butcher T. W.; Amberg W. M.; Hartwig J. F. Angew. Chem. Int. Ed. 2022, 61, e202112251.
[4]	a) Wu T.; Tang W. Chem.-Eur. J. 2021, 27, 3944.
	(b) Pati B. V.; Puthalath N. N.; Banjare S. K.; Nanda T.; Ravikumar P. C. Org. Biomol. Chem. 2023, 21, 2842.
	(c) Lu H.; Yu T. Y.; Xu P. F.; Wei H. Chem. Rev. 2020, 121, 365.
	(d) Bi X.; Zhang Q.; Gu Z. Chin. J. Chem. 2021, 39, 1397.
[5]	a) Deepthi A.; Babu B. P.; Balachandran A. L. Org. Prep. Proced. Int. 2019, 51, 409.
	(b) Kaur N, Grewal P, Poonia, K. Synth. Commun. 2021, 51, 2423.
[6]	a) Pelkey, E T. In Heterocyclic Chemistry, Vol. 11, Eds.Eds.: Gribble, G. W.; Gilchrist, T. L., Elsevier, Oxford, 1999, p. 102.
	(b) Kornfeld E. C.; Jones R. G. J. Org. Chem. 1954, 19, 1671.
[7]	a) Iqbal S.; Rasheed H.; Awan R. J.; Awan R. J.; Mukhtar A.; Moloney M. G. Curr. Org. Chem. 2020, 24, 1196.
	(b) Ferreira V. F.;de Souza, M. C. B. V.; Cunha, A. C.; Pereira, L. O. R.; Ferreira, M. L. G. Org. Prep. Proced. Int. 2001, 33, 411.
[8]	a) Vartanyan R. S. Pharm. Chem. J. 1983, 17, 329.
	(b) Nagai Y.; Uno H.; Umemoto S. Chem. Pharm. Bull. 1977, 25, 1911.
[9]	Zhou W.; Voituriez A. Org. Lett. 2020, 23, 247.
[10]	Chen X. Y.; Enders D. Angew. Chem., Int. Ed. 2019, 58, 6488.
[11]	Lemmerer M.; Schupp M.; Kaiser D.; Maulide N. Nat. Synth. 2022, 1, 923.
[12]	a) Liu C.; Deng Y.; Wang J.; Yang Y.; Tang S.; Lei A. Angew. Chem., Int. Ed. 2011, 50,7337.
	(b) Fujisawa T.; Igeta K.; Odake S.; Morita Y.; Yasuda J.; Morikawa T. Bioorg. Med. Chem. 2002, 10, 2569.
[13]	a) Heravi M. M.; Zadsirjan V.; Kafshdarzadeh K.; Masoumi B. Asian J. Org. Chem. 2020, 9, 1999.
	(b) Stetter H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639.
[14]	a) Jang H. Y.; Hong J. B.; MacMillan D. W. C. J. Am. Chem. Soc. 2007, 129, 7004.
	(b) Clift M. D.; Taylor C. N.; Thomson R. J. Org. Lett. 2007, 9, 4667.
[15]	a) Parida B. B.; Das P. P.; Niocel M.; Cha J. K. Org. Lett. 2013, 15, 1780.
	(b) Shen Z. L.; Goh K. K. K.; Cheong H. L.; Wong C. H. A.; Lai Y. C.; Yang Y. S.; Loh T. P. J. Am. Chem. Soc. 2010, 132, 15852.
	(c) Custar D. W.; Le H.; Morken J. P. Org. Lett. 2010, 12, 3760.
	(d)Xue S.; Li, L. Z.; Liu, Y. K.; Guo, Q. X. J. Org. Chem. 2006, 71, 215.
	(e) Stepherson J. R.; Fronczek F. R.; Kartika R. Chem. Commun. 2016, 52, 2300.
[16]	Kaldre D.; Klose I.; Maulide N. Science 2018, 361, 664.
[17]	Kobatake T.; Yoshida S.; Yorimitsu H.; Oshima K. Angew. Chem., Int. Ed. 2010, 49, 2340.
[18]	Huang S.; Kötzner L.; De C. K.; List B. J. Am. Chem. Soc. 2015, 137, 3446.
[19]	Jadhav A. M.; Gawade S. A.; Vasu D.; Dateer R. B.; Liu R. S. Chem.-Eur. J. 2014, 20, 1813.
[20]	Dong Y.; Li R.; Zhou J.; Sun Z. Org. Lett. 2021, 23, 6387.
[21]	Chen X. Y.; Enders D. Angew. Chem., Int. Ed. 2019, 58, 6488.
[22]	Amaya T.; Maegawa Y.; Masuda T, Osawa T.; Shimizu Y.; Oe Y.; Kobayashi T. J. Am. Chem. Soc. 2015, 137, 10072.
[23]	Lv Y.; Pu W.; Niu J.; Zhao Q.; Wang Z.; Li X. Tetrahedron Lett. 2018, 59, 1497.
[24]	Li Y.; Yang R.; Zhao X.; Yang Y.; Wang Y.; Li Y. Synth. Commun. 2019, 49, 735.

CuI催化C—C键偶联反应构建2-羰基-1,4-二酮

CuI-Catalyzed C—C Bond Coupling Reaction for the Construction of 2-Carbonyl-1,4-diketones

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 3

References 24

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Lanxing Ren, A'na Xu, Xilin Xiao, Hengzhi You, Lijuan Song. Theoretical Study on the Solvent Effect on the Enantioselectivity of Iridium-Catalyzed Asymmetric Hydrogenation Reactions [J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2904-2912.
[2]	Ming Chen, Jing Zhang. Recent Progress in Traceless Directed Functionalization Reactions of Arylcarboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2660-2676.
[3]	Yongbo Tan, Hongbo Shu, Huawen Huang. Recent Advances in Photo-Induced Oxindole Formation from N-Arylacrylamides [J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 2086-2108.
[4]	Shuang Wang, Yangjie Mao, Shaojie Lou, Danqian Xu. Recent Advances in Asymmetric C—H Bond Functionalization Using Oxidizing Directing Groups [J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 1961-1994.
[5]	Shunxi Li, Lixu You, Yulong Li, Wei Shu. Recent Progress on Light-Mediated C—N Bond-Forming Processes from Ammonia and Equivalents [J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1460-1477.
[6]	Haoyan Wu, Mingyue He, Jun'an Ma, Faguang Zhang. Recent Advances in Photochemical Reactions Enabled by Triarylamine [J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1634-1643.
[7]	Xun Tian, Guogang Deng, Xiaodong Yang. Progress on Cobalt-Catalyzed C(sp²)—H Activation for the Construction of Nitrogen-Containing Benzo Heterocycles [J]. Chinese Journal of Organic Chemistry, 2025, 45(2): 655-667.
[8]	Tianpeng Ling, Haitao Qin, Feng Liu. Recent Advances in Enantioselective Radical Reactions of C(sp³)—H Bond [J]. Chinese Journal of Organic Chemistry, 2025, 45(2): 498-515.
[9]	Yu'nan Zhu, Weikang Jiao, Xuebai Wei, Chunhua Chen, Dongliang Mo. Recent Progress in Radical Arylation Reaction Involving Diaryliodonium Salts [J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3672-3690.
[10]	Zijie Li, Zheng Hao, Shengyuan Yang, Wenchao Yang, Tao Jin. Recent Advances in the Radical Reactions of Dihydroquinazolinone Derivatives [J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3644-3654.
[11]	Zhouting Zeng, Huaixin Wei, Wei-Min He, Mingming Yu, Zu-Li Wang, Jinhui Cai. Synthesis of Selenylated Maleimides and Alkenes via Bromide Catalysis [J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3786-3796.
[12]	Huiying Liu, Zhongtian Wu, Haotian Li, Xinxin Wu. Cu-Catalyzed Regioselective Heteroarylation of C(sp³)—H Bond Induce by Sulfonyl Group [J]. Chinese Journal of Organic Chemistry, 2025, 45(1): 297-306.
[13]	Jia-Xi Jiang, Quan-Zhong Liu. Non-Metallic Carbene Pathway Transformations of Vinyl Diazo Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2640-2657.
[14]	Zhaoyang Zhang, Weiwei Luo, Jun Zhou. Research Progress of Radical Reactions Involving Silyl Enol Ethers [J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2658-2681.
[15]	Chen-Long Li, Zhi-Xiang Yu. Progress in Transition-Metal-Catalyzed Carbonylative Cycloadditions Using Carbon Monoxide [J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1045-1068.