双环[1.1.0]丁烷合成策略的研究进展

doi:10.12461/PKU.DXHX202508027

Abstract

Abstract: Bicyclo[1.1.0]butane (BCB), one of the smallest bridged-ring compounds, possesses remarkable ring strain and distinctive reactivity. As a valuable organic scaffold for constructing functionalized small molecules, BCB has garnered significant attention in both medicinal and synthetic chemistry. This review systematically summarizes the principal synthetic approaches to BCBs, classifying them into three categories: substitution reactions, insertion reactions, and rearrangement reactions. The discussion encompasses representative methodologies from classical procedures to cutting-edge developments. These synthetic strategies demonstrate diverse construction pathways and innovative design concepts, which can stimulate students' interest and enhance their structural thinking. Serving as a bridge between textbook knowledge and frontier research, this work provides valuable reference materials for organic synthesis education and research training and presents selected case studies to facilitate the overcoming of teaching challenges and the cultivation of critical thinking skills in classroom settings.

Key words: Bicyclo[1.1.0]butane, Organic synthesis, Organic synthesis education

Baitong Wei, Rongxiu Zhu, Zhenghu Xu. Advances in the synthetic strategies of bicyclo[1.1.0]butane[J].University Chemistry, 2026, 41(9): 162-172.

References

[1] C.B. Kelly, J.A. Milligan, L.J. Tilley, T.M. Sodano, Chem. Sci. 2022, 13, 11721.
[2] K.B. Wiberg, G.M. Lampman, R.P. Ciula, D.S. Connor, P. Schertler, J. Lavanish, Tetrahedron 1965, 21, 2749.
[3] J.C. Hearn, B.M. Rice, B.C. Barnes, P.W. Chung, J. Phys. Chem. A. 2024, 128(35), 7489.
[4] I.R. Ramazanov, A.V. Yaroslavova, U.M. Dzhemilev, Russ. Chem. Rev. 2012, 81(8), 700.
[5] M. Golfmann, J.C.L. Walker, Commun. Chem. 2023, 6, 9.
[6] 王彦广, 惠新平, 丁玉强, 刘晨江, 陆展. 大学化学, 2025, 40(2), 151.
[7] K.B. Wiberg, R.P. Ciula, J. Am. Chem. Soc. 1959, 81(19), 5261.
[8] M. Jung, V.N.G. Lindsay, J. Am. Chem. Soc. 2022, 144(11), 4764.
[9] J.E. Muir, M. Jung, V.N.G. Lindsay, Org. Synth. 2025, 102, 185.
[10] Y. Gaoni, Tetrahedron Lett. 1981, 22(43), 4339.
[11] Z. Zhong, B. Brown, T.-K. Ma, D.J. Mann, A. Armstrong, J.A. Bull, Angew. Chem., Int. Ed. 2025, 64(5), e202420028.
[12] N.O. Nilsen, L. Skattebøl, M.S. Baird, S.R. Buxton, P.D. Slowey, Tetrahedron Lett. 1984, 25(27), 2887.
[13] R.E. McNamee, M.M. Haugland, J. Nugent, R. Chan, K.E. Christensen, E.A. Anderson, Chem. Sci. 2021, 12, 7480.
[14] W.R. Moore, K.G. Taylor, P. Miiller, S.S. Hall, Z.L.F. Gaibel, Tetrahedron Lett. 1970, 11(27), 2365.
[15] D.M. Lemal, F. Menger, G.W. Clark, J. Am. Chem. Soc. 1963, 85(16), 2529.
[16] K. Chen, X. Huang, S.B.J. Kan, R.K. Zhang, F.H. Arnold, Science 2018, 360, 71.
[17] M.D. Mandler, J. Mignone, E.A. Jurica, M.D. Palkowitz, D. Aulakh, A.N. Cauley, C.A. Farley, S. Zhang, S.C. Traeger, A. Sarjeant, et al., Org. Lett. 2023, 25(44), 7947.
[18] C.B. Kelly, A.M. Colthart, B.D. Constant, S.R. Corning, L.N.E. Dubois, J.T. Genovese, J.L. Radziewicz, E.M. Sletten, K.R. Whitaker, L. Tilley, J. Org. Lett. 2011, 13(7), 1646.
[19] Y. Gaoni, Tetrahedron Lett. 1976, 17(6), 503.
[20] L. Thai-Savard, A.B.; Charette, Chem. Commun. 2023, 59, 5273.
[21] R. Suresh, N. Orbach, I. Marek, J. Am. Chem. Soc. 2024, 146(20), 13748.
[22] B.D. Schwartz, M.Y. Zhang, R.H. Attard, M.G. Gardiner, L.R. Malins, Chem. Eur. J. 2020, 26, 2808.
[23] R.E. McNamee, A.L. Thompson, E.A. Anderson, J. Am. Chem. Soc. 2021, 143(50), 21246.
[24] R.E. McNamee, A. Dasgupta, K.E. Christensen, E.A. Anderson, Org. Lett. 2024, 26(1), 360.
[25] C. Qin, H.M.L. Davies, Org. Lett. 2013, 15(2), 310.
[26] R. Panish, S.R. Chintala, D.T. Boruta, Y. Fang, M.T. Taylor, J.M. Fox, J. Am. Chem. Soc. 2013, 135(25), 9283.
[27] K.B. Wiberg, N. McMurdie, J. Org. Chem. 1993, 58, 5603.
[28] M. Pitchai, K.C. Nanjundaswamy, S. Ulaganathan, M. Javeed, A. Ramirez, P. Srinivas, S. Roy, S.C. Traeger, J. Mignone, E.A. Jurica, et al., J. Org. Chem. 2025, 90(9), 3468.

Advances in the synthetic strategies of bicyclo[1.1.0]butane

PDF

Like

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Metrics

Recommended 0

[1]	Yongqiang Zhang. Mechanism-first and performance-based assessment: teaching reform and practice in the graduate advanced organic synthesis course [J]. University Chemistry, 2026, 41(9): 11-17.
[2]	Yinuo Wang, Yichen Gan, Keyu Li, Dazhen Xu. Synthesis of 2-(4-Chlorobenzylidene) malononitrile via a self-made continuous flow reactor: a proposed comprehensive chemistry experiment [J]. University Chemistry, 2026, 41(7): 319-325.
[3]	Dengke Ma. Application of Integrating Fundamental Knowledge and Cutting-Edge Developments in the Teaching of Organic Synthesis: Taking the Asymmetric Meinwald Rearrangement as an Example [J]. University Chemistry, 2026, 41(4): 67-74.
[4]	Ruoyu Cao, Jiaxin Chen, Jiaen Hu, Youting Zhai, Jiacong Fu, Lifen Hou, Xuebin Yan, Yanyang Li, Kai Li, Shuangquan Zang. Interactive Digital Experiment for Organic Synthesis: Designing Process and Case Presentation [J]. University Chemistry, 2026, 41(1): 406-412.
[5]	Yifei Li, Xuexin Chen, Sihan Liu, Shiyi Chen, Ling Pan. Design and Application of Chemical Analysis Platform Based on Intelligent Integration of Big Data and Deep Learning Algorithm in Undergraduate Experimental Teaching [J]. University Chemistry, 2026, 41(1): 169-178.
[6]	Fengxiao Wang, Zhiwei Miao, Yaofeng Yuan. Organophosphorus Chemistry and Its Integration in Teaching of Chemistry [J]. University Chemistry, 2025, 40(8): 158-168.
[7]	Shuhui Li, Rongxiuyuan Huang, Yingming Pan. Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment [J]. University Chemistry, 2025, 40(5): 357-365.
[8]	Yongjian Zhang, Fangling Gao, Hong Yan, Keyin Ye. Electrochemical Transformation of Organosulfur Compounds [J]. University Chemistry, 2025, 40(5): 311-317.
[9]	Zhongming Song, Xingting Ma, Shuqing Li, Shengran A, Yuyang Zhang, Jing Tang, Yue Yao, Yueyuan Mao, Shengbiao Zheng, Wanwan Yao. Synthesis and Characterization of Iridium Complex: A Comprehensive Chemistry Experiment [J]. University Chemistry, 2025, 40(2): 278-288.
[10]	Chengzhuo Zhou, Zhaojun Xie. Exploring the Application of Artificial Intelligence Prediction Models in Organic Chemistry Laboratory Teaching: A Preliminary Study [J]. University Chemistry, 2025, 40(2): 320-331.
[11]	Yinuo Wang, Ziyu Liu, Hongxia Tan, Jun Tong, Dazhen Xu. Synthesis of Bromobenzoxazine: Introduce a Comprehensive Organic Chemistry Experiment Transformed from Undergraduate Research Innovation [J]. University Chemistry, 2025, 40(10): 208-216.
[12]	Ge Zhang, Min Ren, Yue Wang. Ideological and Political Education Design in Organic Synthesis Chemistry Course Based on Deep Learning: A Case Study of “Radical Reactions and Their Applications” [J]. University Chemistry, 2025, 40(1): 91-98.
[13]	Hong He, Xiadie Wu, Zhongwei Hou, Lei Wang. Recent Advances in the Electrochemical Aziridination of Alkenes [J]. University Chemistry, 2025, 40(1): 196-205.
[14]	Kexin Ma, Jiawei Fei, Yumei Lin. The History and Progress of Antiaromatic Compounds [J]. University Chemistry, 2025, 40(1): 219-226.
[15]	Aidang Lu, Yunting Liu, Yanjun Jiang. Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds [J]. University Chemistry, 2024, 39(8): 241-246.