Copper-Catalyzed Cyclization of 1-Aryl-1-cycloalcohols and 1,3-Dicarbonyl Compounds: Synthesis of Cycloalkane-Fused Dihydrofuran Derivatives

doi:10.6023/cjoc201903040

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (8): 2226-2234.DOI: 10.6023/cjoc201903040 Previous Articles Next Articles

Special Issue: 陈茹玉先生诞辰100周年

Articles

铜催化1-芳基-1-环醇和1,3-二羰基化合物的环化反应:合成环烷烃稠合的二氢呋喃衍生物

杨胜彪^a, 李燕^a, 张前^a,b

a 东北师范大学化学学院长春 130024;
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

收稿日期:2019-03-21 修回日期:2019-05-16 发布日期:2019-05-21
通讯作者: 李燕, 张前 E-mail:liy078@nenu.edu.cn;zhangq651@nenu.edu.cn
基金资助:
国家自然科学基金（No.21831002）和万人计划资助项目.

Copper-Catalyzed Cyclization of 1-Aryl-1-cycloalcohols and 1,3-Dicarbonyl Compounds: Synthesis of Cycloalkane-Fused Dihydrofuran Derivatives

Yang Shengbiao^a, Li Yan^a, Zhang Qian^a,b

a Department of Chemistry, Northeast Normal University, Changchun 130024;
b State Key Laboratory of Organometallic Chemistry, Shang Hai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2019-03-21 Revised:2019-05-16 Published:2019-05-21
Contact: 10.6023/cjoc201903040 E-mail:liy078@nenu.edu.cn;zhangq651@nenu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21831002) and Ten Thousand Talents Program.

1. Copper-Catalyzed Cyclization of 1-Aryl-1-cycloalcohols and 1,3-Dicarbonyl Compounds: Synthesis of Cycloalkane-Fused Dihydrofuran Derivatives.PDF(5117KB)

Abstract

A novel method of copper-catalyzed cyclization of 1-aryl-1-cycloalcohols and 1,3-dicarbonyl compounds has been developed, affording various cycloalkane-fused dihydrofurans in moderate to excellent yields. This transformation proceeds under mild conditions and with a good tolerance of functional groups. The mechanistic investigation revealed that the reaction involved radical intermediates.

Key words: cyclization, cycloalcohol, 1,3-dicarbonyl compound, dihydrofuran

Cite this article

Yang Shengbiao, Li Yan, Zhang Qian. Copper-Catalyzed Cyclization of 1-Aryl-1-cycloalcohols and 1,3-Dicarbonyl Compounds: Synthesis of Cycloalkane-Fused Dihydrofuran Derivatives[J]. Chinese Journal of Organic Chemistry, 2019, 39(8): 2226-2234.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Nakashima, K.; Masayoshi Oyama, M.; Ito, T.; Akao, Y.; Witono, J. R.; Darnaedi, D.; Tanaka, T.; Murata, J.; Iinuma, M. Tetrahedron 2012, 68, 2421.
[2] Lallemand, J.-Y.; Six, Y.; Ricard, L. Eur. J. Org. Chem. 2002, 503.
[3] Baraza, L. D.; Joseph, C. C.; Nkunya, M. H. Nat. Prod. Res. 2007, 21, 1027.
[4] Ghosh, A. K.; Parham, G. L.; Martyr, C. D.; Nyalapatla, P. R.; Osswald, H. L.; Agniswamy, J.; Wang, Y.-F.; Amano, M.; Weber, I. T.; Mitsuya, H. J. Med. Chem. 2013, 56, 6792.
[5] (a) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519.
(b) Lee, Y. R.; Kim, B. S.; Kim, D. H. Tetrahedron 2000, 56, 8845.
(c) Pan, X.-Q.; Zou, J.-P.; Zhang, W. Mol. Diversity 2009, 13, 421.
(d) Liu, X.; Chen, X.; Mohr, J. T. Chem.-Eur. J. 2016, 22, 2274.
(e) Calter, M. A.; Phillips, R. M.; Flaschenriem, C. J. Am. Chem. Soc. 2005, 127, 14566.
(f) Chennapuram, M.; Emmadi, N. R.; Bingi, C.; Nanubolu, J. B.; Atmakur, K. Green Chem. 2014, 16, 3237.
(g) Chawla, R.; Singh, A. K.; Yadav, L. D. S. Tetrahedron Lett. 2012, 53, 3382.
[6] (a) Mekonnen, A.; Carlson, R. Synthesis 2006, 1657.
(b) Zhong, C.; Liao, T.; Tuguldur, O.; Shi, X. Org. Lett. 2010, 12, 2064.
(c) Heiba, E.-A. I.; Dessau, R. M. J. Org. Chem. 1974, 39, 3456.
(d) Riveira, M. J.; Mischne, M. P. J. Org. Chem. 2014, 79, 8244.
(e) Zhang, Z.; Li, C.; Wang, S. H.; Zhang, F. M.; Han, X.; Tu, Y. Q.; Zhang, X. M. Org. Biomol. Chem. 2017, 15, 3239.
[7] (a) Karade, N. N.; Shirodkar, S. G.; Patil, M. N.; Potrekar, R. A.; Karade, H. N. Tetrahedron Lett. 2003, 44, 6729.
(b) Nishino, H.; Fujino, R. Synthesis 2005, 731.
(c) Yilmaz, M.; Pekel, A. T. J. Fluorine Chem. 2011, 132, 628.
(d) Dengiz, C.; Caliskan, R.; Balci, M. Tetrahedron Lett. 2012, 53, 550.
(e) Yirsaw, A. M.; Carlson, R. E. ARKIVOC 2017, iv, 74.
(f) Lal, S.; Chowdhury, A.; Namboothiri, I. N. N. Tetrahedron 2017, 73, 1297.
[8] Ye, S.; Yu, Z.-X. Chem. Commun. 2011, 47, 794.
[9] CCDC 1589697(6e) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
[10] (a) Wang, H.; Guo, L.-N.; Duan, X.-H. Org. Lett. 2013, 15, 5254.
(b) Wang, G.-W.; Dong, Y.-W.; Wu, P.; Yuan, T.-T.; Shen, Y.-B. J. Org. Chem. 2008, 73, 7088.
(c) Li, P.; Zhao, J.; Xia, C.; Li, F. Org. Lett. 2014, 16, 5992.
(d) Casey, B. M.; Eakin, C. A.; Jiao, J.; Sadasivam, D. V.; Flowers, R. A. Tetrahedron 2009, 65, 10762.
(e) Yi, H.; Liao, Z.; Zhang, G; Zhang, G.; Fan, C.; Zhang, X.; Bunel, E. E.; Pao, C. W.; Lee, J. F.; Lei, A. Chem.-Eur. J. 2015, 21, 18925.

[1]	Baochang Gao, Yu Shi, Yuan Tian, Zhiguo Zhang, Jingru Zhang, Yufeng Sun, Guoliang Mao, Lingyan Dai. Synthesis of 4-Methyl-2-oxo-6-arylamino-2H-pyran-3-carbonitrile Derivatives [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 644-649.
[2]	Jing Tang, Wenkun Luo, Jun Zhou. Advances in the Synthesis of Azaspiro[4.5]trienones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3006-3034.
[3]	Yingke Feng, He Wang, Mengxing Cui, Ran Sun, Xin Wang, Yang Chen, Lei Li. Visible-Light-Induced Difluoroalkylated Cyclization of Novel Functionalized Aromatic Isocyanides [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2913-2925.
[4]	Yuzhuo Chen, Hongmei Sun, Liang Wang, Fangzhi Hu, Shuaishuai Li. Research Progress on Construction of Heterocyclic Skeletons Based on α-Hydride Transfer Strategy [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2323-2337.
[5]	Lixing Sun, Tingting Sun, Haiqing Wang, Shufang Wu, Xiaoye Wang, Tianya Liu, Yuchen Zhang. Lewis Acid-Catalyzed [2+4] Cyclization of 3-Alkyl-2-vinylindoles with α,β-Unsaturated N-Sulfonyl Ketimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2178-2188.
[6]	Zhijun Ren, Weiwei Luo, Jun Zhou. Recent Progress in Silver-Mediated Tandem Cyclization of N-Arylacrylamides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2026-2039.
[7]	Rongbin Cai, Bing Li, Qi Zhou, Longyi Zhu, Jun Luo. Synthesis of 4,8,9,10-Tetrafunctionalized 2-Azaadamantanes and Their 2-Azaprotoadamantane Skeleton Isomers [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2217-2225.
[8]	Jingpeng Li, Shuntao Huang, Qi Yang, Weiqiang Li, Teng Liu, Chao Huang. A Practical Synthesis of (Z)-N-Vinyl Substituted N,O-Acetals under Continuous Flow Technology [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1550-1558.
[9]	Nan Jiang, Guanjie Huang, Yan Hu, Bo Wang. Ruthenium-Catalyzed C—H [4＋2] Annulation of Quinazolinones with Vinylene Carbonate [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1537-1549.
[10]	Wenting Wei, Zhuangzhuang Li, Wandi Li, Jiaqi Li, Xianying Shi. Green Method for Constructing Phthalides via Oxidative Coupling of Aromatic Acids and Acrylates in Neat Water and Air [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1177-1186.
[11]	Zhen Tang, Chao Pi, Yangjie Wu, Xiuling Cui. Rhodium-Catalyzed Tandem Acylmethylation/Annulation Reactions of 2-Aryl-2H-indazoles with Sulfoxonium Ylides: Easy Access to 6-Arylindazolo[2,3-a]quinolines [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1187-1196.
[12]	Chengfu Zeng, Yuan He, Qing Li, Lin Dong. Ir(III)-Catalyzed Novel Three-Component Cascade Trifluoroethoxylation and One-Pot Method to Construct Complex Amide Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1115-1123.
[13]	Haiqing Wang, Shuang Yang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 974-999.
[14]	Jinxiao Zhao, Tonghui Wei, Sen Ke, Yi Li. Visible Light-Catalyzed Synthesis of Difluoroalkylated Polycyclic Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1102-1114.
[15]	Donghan Liu, Xihang Lu, Zhangmengjie Chai, Haoqi Yang, Yulin Sun, Fuchao Yu. Progress in Construction of 2H-Pyrrol-2-ones Skeleton [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 57-73.

铜催化1-芳基-1-环醇和1,3-二羰基化合物的环化反应:合成环烷烃稠合的二氢呋喃衍生物

Copper-Catalyzed Cyclization of 1-Aryl-1-cycloalcohols and 1,3-Dicarbonyl Compounds: Synthesis of Cycloalkane-Fused Dihydrofuran Derivatives

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments