光诱导重氮酸酯与偕二氟烯烃[1 + 2]环加成合成二氟环丙烷

doi:10.6023/cjoc202406027

有机化学

研究论文

光诱导重氮酸酯与偕二氟烯烃[1 + 2]环加成合成二氟环丙烷

慕晓楠^a,b, 管敏慧^b, 牛雨龙^b, 陈浩^b,*, 李传莹^a,*, 王磊^b,c,*

^a浙江理工大学化学系杭州 310018;
^b台州学院高研院和药学院台州 318000;
^c杭州师范大学材料与化学化工学院,有机硅化学及材料技术教育部重点实验室杭州 311121

收稿日期:2024-06-20 修回日期:2024-07-25
基金资助:
国家自然科学基金 (No. 22071171)和浙江省自然科学基金(LZ22B020003)资助项目.

Synthesis of difluorocyclopropanes via a photoinduced [1 + 2] cycloaddition of diazo esters with gem-difluoroalkenes

Xiaonan Mu^a,b, Minhui Guan^b, Yulong Niu^b, Hao Chen^b,*, Chuanying Li^a,*, Lei Wang^b,c,*

^aDepartment of Chemistry, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018, P. R. China;
^bAdvanced Research Institute & School of Pharmaceutical Sciences, Taizhou University,Taizhou, Zhejiang 318000, P. R. China;
^bCollege of Material Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, 311121, Zhejiang, P. R. China

Received:2024-06-20 Revised:2024-07-25
Contact: *E-mail: licy@zstu.edu.cn; leiwang88@hotmail.com; haochenchemical@163.com
Supported by:
National Natural Science Foundation of China (22071171) and the Natural Science Foundation of Zhejiang Province (LZ22B020003)

文章分享

摘要/Abstract

在可见光促进下,偕二氟烯烃与芳基重氮酸酯的[1 + 2]环加成为合成1,1-偕二氟环丙烷提供了一条有效而重要的途径。反应条件温和,操作简单。系列重氮酸酯和偕二氟烯烃都能适用于该反应(36个例子),并以良好的收率和优异的非对映选择性(> 20:1)得到相应的目标产物。

关键词: 有机光催化, 偕二氟烯烃, 重氮酸酯, [1+2]环加成, 1,1-偕二氟环丙烷

A visible-light-promoted [1 + 2] cycloaddition of gem-difluoroalkenes with aryl diazo esters provides an efficient and important route to 1,1-difluorocyclopropanes. The reaction conditions are mild, and the operation is very simple. A number of diazo esters and gem-difluoroalkenes are suitable for this reaction (36 examples), providing the desired products in good yields with excellent diastereoselectivity (> 20: 1).

Key words: Organic photochemistry, gem-difluoroalkenes, diazo esters, [1 + 2] cycloaddition, 1,1-difluorocyclopropanes

引用此文

慕晓楠, 管敏慧, 牛雨龙, 陈浩, 李传莹, 王磊. 光诱导重氮酸酯与偕二氟烯烃[1 + 2]环加成合成二氟环丙烷[J]. 有机化学, doi: 10.6023/cjoc202406027.

Xiaonan Mu, Minhui Guan, Yulong Niu, Hao Chen, Chuanying Li, Lei Wang. Synthesis of difluorocyclopropanes via a photoinduced [1 + 2] cycloaddition of diazo esters with gem-difluoroalkenes[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202406027.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881; (b) Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Acenña, J. L.; Soloshonok, V. A.; Izawa, K.; Liu, H. Chem. Rev. 2016, 116, 422; (c) Moschner, J.; Stulberg, V.; Fernandes, R.; Huhmann, S.; Leppkes, J.; Koksch, B. Chem. Rev. 2019, 119, 10718; (d) Zhang, C.; Yan, K.; Fu, C.; Peng, H.; Hawker, C. J.; Whittaker, A. K. Chem. Rev. 2022, 122, 167; (e) Preshlock, S.; Tredwell, M.; Gouverneur, V. Chem. Rev. 2016, 116, 719.
[2] Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320; (b) O’Hagan, D.; Deng, H. Chem. Rev. 2015, 115, 634; (c) Shao, Q.; Huang, Y. Chem. Commun. 2015, 51, 6584; (d) Couve-Bonnaire, S.; Cahard, D.; Pannecoucke, X. Org. Biomol. Chem. 2007, 5, 1151.
[3] Talele, T. T. J. Med. Chem. 2016, 59, 8712; (b) Burch, J. D.; Barrett, K.; Chen, Y.; DeVoss, J.; Eigenbrot, C.; Goldsmith, R.; Ismaili, M. H. A.; Lau, K.; Lin, Z.; Ortwine, D. F.; Zarrin, A. A.; McEwan, P. A.; Barker, J. J.; Ellebrandt, C.; Kordt, D.; Stein, D. B.; Wang, X.; Chen, Y.; Hu, B.; Xu, X.; Yuen, P.-W.; Zhang, Y.; Pei, Z. J. Med. Chem. 2015, 58, 3806; (c) Nicolaou, K. C.; Shelke, Y. G.; Dherange, B. D.; Kempema, A.; Lin, B.; Gu, C.; Sandoval, J.; Hammond, M.; Aujay, M.; Gavrilyuk, J. J. Org. Chem. 2020, 85, 2865; (d) Dolbier, W. R.; Battiste, M. A. Chem. Rev. 2003, 103, 1071; (e) Li, L.; Wang, F.; Ni, C.; Hu, J. Angew. Chem. Int. Ed. 2013, 52, 12390.
[4] Wang, J.; Blaszczyk, S. A.; Li, X.; Tang, W. Chem. Rev. 2021, 121, 110; (b) Dolbier, W. R.; Battiste, M. A. Chem. Rev. 2003, 103, 1071; (c) Fedoryński, M. Chem. Rev. 2003, 103, 1099; (d) Munemori, D.; Narita, K.; Nokami, T.; Itoh, T. Org. Lett. 2014, 16, 2638; (e) Kageshima, Y.; Suzuki, C.; Oshiro, K.; Amii, H. Synlett 2015, 63; (f) Nihei, T.; Hoshino, T.; Konno, T. Org. Lett. 2014, 16, 4170.
[5] Xu, J.; Ahmed, E.-A.; Xiao, B.; Lu, Q.-Q.; Wang, Y.-L.; Yu, C.-G.; Fu, Y. Angew. Chem. Int. Ed. 2015, 54, 8231; (b) Pigeon, X.; Bergeron, M.; Barab, F.; Dub, P.; Frost, H. N.; Paquin, J.-F. Angew. Chem. Int. Ed. 2010, 49, 1123; (c) Lv, L.; Li, C.-J. Angew. Chem. Int. Ed. 2021, 60, 13098; (d) Lv, L.; Qian, H.; Ma, Y.; Huang, S.; Yan, X.; Li, Z. Chem. Sci. 2021, 12, 15511; (e) Yuan, W.; Li, X.; Qi, Z.; Li, X. Org. Lett. 2022, 24, 2093; (f) Jiang, Z.-T.; Huang, J.; Zeng, Y.; Hu, F.; Xia, Y. Angew. Chem. Int. Ed. 2021, 60, 10626; (g) Sun, C.; Zhou, Q.; Li, C.-Y.; Hou, Z.-W.; Wang, L. Org. Lett. 2024, 26, 883; (h) Shen, M.; Li, L.; Zhou, Q.; Wang, J.; Wang, L. Chin. J. Org. Chem. 2023, 43, 697; (i) Wang, F.; Wang, L. Chin. J. Org. Chem. 2023, 43, 4157; (j) Gao, R.; Zuo, L.; Wang, F.; Li, C.-Y.; Jiang, H.; Li, P.; Wang, L. Chin. J. Org. Chem. 2022, 42, 1883.
[6] Boger, D. L.; Jenkins, T. J. J. Am. Chem. Soc. 1996, 118, 8860; (b) Wang, F.; Luo, T.; Hu, J.; Wang, Y.; Krishnan, H. S.; Jog, P. V.; Ganesh, S. K.; Prakash, G. K. S.; Olah, G. A. Angew. Chem. Int. Ed. 2011, 50, 7153; (c) Hryshchuk, O. V.; Varenyk, A. O.; Yurov, Y.; Kuchkovska, Y. O.; Tymtsunik, A. V.; Grygorenko, O. O. Eur. J. Org. Chem. 2020, 15, 2217; (d) Louis-Goff, T.; Trinh, H. V.; Chen, E.; Rheingold, A. L.; Ehm, C.; Hyvl, J. ACS Catal. 2022, 12, 3719; (e) Eusterwiemann, S.; Martinez, H.; Dolbier, W. R. J. Org. Chem. 2012, 77, 5461.
[7] Yamani, K.; Pierre, H.; Archambeau, A.; Meyer, C.; Cossy, J. Angew. Chem. Int. Ed. 2020, 59, 18505; (b) Sekine, K.; Ushiyama, A.; Endo, Y.; Mikami, K. J. Org. Chem. 2020, 85, 7916; (c) Jiang, Z.-T.; Chen, Z.; Zeng, Y.; Shi, J.-L.; Xia, Y. Org. Lett. 2022, 24, 6176; (d) Zhang, Z.; Gevorgyan, V. J. Am. Chem. Soc. 2022, 144, 20875; (e) Xu, H.; Fang, X. J.; Huang, W. S.; Xu, Z.; Li, L.; Ye, F.; Cao, J.; Xu, L. W. Org. Chem. Front. 2022, 9, 5272.
[8] Xia, Y.; Qiu, D.; Wang, J. Chem. Rev. 2017, 117, 13810; (b) Chen, J.; Shen, X.; Lu, Z. J. Am. Chem. Soc. 2020, 142, 14455; (c) Chen, Q.; Li, K.; Lu, T.; Zhou, Q. RSC Adv. 2016, 6, 24792; (d) Zhou, P.-X.; Zhou, Z.-Z.; Chen, Z.-S.; Ye, Y.-Y.; Zhao, L.-B.; Yang, Y.-F.; Xia, X.-F.; Luo, J.-Y.; Liang, Y.-M. Chem. Commun. 2013, 49, 561; (e) Tan, F.; Pu, M.; He, J.; Li, J.; Yang, J.; Dong, S.; Liu, X.; Wu, Y.-D.; Feng, X. J. Am. Chem. Soc. 2021, 143, 2394; (f) Xia, Y.; Liu, Z.; Liu, Z.; Ge, R.; Ye, F.; Hossain, M.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2014, 136, 3013.
[9] Yang, J. H.; Wang, J. Z.; Huang, H. T.; Qin, G. P.; Jiang, Y. B.; Xiao, T. B. Org. Lett. 2019, 21, 2654; (b) Jana, S.; Yang, Z.; Li, F.; Empel, C.; Ho, J. M.; Koenigs, R. M. Angew. Chem. Int. Ed. 2020, 59, 5562; (c) Zhang, Z.; Zhou, Y.; Wang, J.; Zhang, Y.; Wang, L.; Liu, J.; Zhou, C.; Wang, M.; Li, P. Org. Biomol. Chem., 2024, 22, 1708.
[10] Jurberg, I. D.; Davies, H. M. L. Chem. Sci. 2018, 9, 5112; (b) Fischer, S.; Nguyen, T.-T. H.; Ratzenboeck, A.; Davies, H. M. L.; Reiser, O. Org. Lett. 2023, 25, 4411; (c) George, V.; König, B. Chem. Commun. 2023, 59, 11835; (d) Zhao, S.; Chen, X.-X.; Gao, N.; Qian, M.; Chen, X. J. Org. Chem. 2021, 86, 7131; (e) Xia, D. D.; Wu, R. K.; Wang, J. X.; Han, X. Y.; Li, Y. C.; Li, Q. N.; Luan, X.; Hong, X.; Zhang, Y.; Zhang, W.-D. ACS Catal. 2023, 13, 9806.
[11] Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.-M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119; (b) Lindsay, V. N. G.; Fiset, D.; Gritsch, P. J.; Azzi, S.; Charette, A. B. J. Am. Chem. Soc. 2013, 135, 1463; (c) Doyle, M. P.; Davies, S. B.; Hu, W. Chem. Commun. 2000, 867; (d) S.; Zhu, J. A.; Perman, Zhang, X. P. Angew. Chem. Int. Ed. 2008, 47, 8460; (e) Xie, M.-S.; Zhou, P.; Niu, H.-Y.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2016, 18, 4344.
[12] Hommelsheim, R.; Guo, Y.; Yang, Z.; Empel, C.; Koenigs, R. M. Angew. Chem. Int. Ed. 2019, 58, 1203; (b) Saha, A.; Sen, C.; Guin, S.; Das, C.; Maiti, D.; Sen, S.; Maiti, D. Angew. Chem. Int. Ed. 2023, 62, e202308916.
[13] Hu, J.; Han, X.; Yuan, Y.; Shi, Z. Angew. Chem. Int. Ed. 2017, 56, 13342; (b) Xie, J.; Yu, J.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Angew. Chem. Int. Ed. 2016, 55, 9416; (c) Wu, F.-P.; Yuan, Y.; Liu, J.; Wu, X.-F. Angew. Chem. Int. Ed. 2021, 60, 8818; (d) Lu, X.; Wang, Y.; Zhang, B.; Pi, J.-J.; Wang, X.-X.; Gong, T.-J.; Xiao, B.; Fu, Y. J. Am. Chem. Soc. 2017, 139, 12632; (e) Xie, S.-L.; Gao, X.-T.; Wu, H.-H.; Zhou, F.; Zhou, J. Org. Lett. 2020, 22, 8424; (f) Zhu, C.; Zhang, Y.-F.; Liu, Z.-Y.; Zhou, L.; Liu, H.; Feng, C. Chem. Sci. 2019, 10, 6721.
[14] Liu, J.; Yu, L.; Zheng, C.; Zhao, G. Angew. Chem. Int. Ed. 2021, 60, 23641; (b) Zhu, C.; Song, S.; Zhou, L.; Wang, D.-X.; Feng, C.; Loh, T.-P. Chem. Commun. 2017, 53, 9482; (c) Orsi, D. L.; Douglas, J. T.; Sorrentino, J. P.; Altman, R. A. J. Org. Chem. 2020, 85, 10451; (d) Bai, D.; Wu, F.; Chang, L.; Wang, M.; Wu, H.; Chang, J. Angew. Chem. Int. Ed. 2022, 61, e202114918.
[15] Du, D.; Ji, C.; Zheng, S.; Chen, Y.; Cai, H.; Li, Z.; Yan, D.; Teng, H. Adv. Synth. Catal. 2024, 366, DOI:10.1002/adsc.202301401.
[16] Xu, B.; Troian-Gautier, L.; Dykstra, R.; Martin, R. T.; Gutierrez, O.; Tambar, U. K. J. Am. Chem. Soc. 2020, 142, 6206; (b) Y.; Empel, Guo, C.; Pei, C.; Atodiresei, I.; Fallon, T.; Koenigs, R. M. Org. Lett. 2020, 22, 5126.

光诱导重氮酸酯与偕二氟烯烃[1 + 2]环加成合成二氟环丙烷

Synthesis of difluorocyclopropanes via a photoinduced [1 + 2] cycloaddition of diazo esters with gem-difluoroalkenes

PDF

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 8

编辑推荐

相关统计

本文评价

[1]	孙超, 周泉, 李传莹, 王磊. 苯并唑-氮杂环卡宾钯配合物的合成表征及应用[J]. 有机化学, 2024, 44(6): 1957-1966.
[2]	曹香雪, 贾雅会, 殷世纪, 徐亮, 韦玉, 宋欢欢. 可见光诱导二氢喹唑啉酮碳碳键断裂与三氟甲基取代烯烃的脱氟烷基化反应研究[J]. 有机化学, 2024, 44(5): 1549-1557.
[3]	沈都益, 李玲慧, 靳鸽, 梁雨佳, 张欣慧, 公培伟, 张范军, 晁绵冉. 基于单电子转移的黄素仿生光催化氧化研究进展[J]. 有机化学, 2024, 44(4): 1069-1093.
[4]	陈祥, 欧阳文韬, 李潇, 何卫民. 可见光诱导有机光催化合成二氟乙基苯并噁嗪[J]. 有机化学, 2023, 43(12): 4213-4219.
[5]	李文娟, 张睿, 蔡志华, 韩小强, 何林, 代斌. 苯炔[3+2]环加成反应构建三氟甲基取代的苯并环状亚砜亚胺衍生物及其杀棉蚜活性研究[J]. 有机化学, 2022, 42(9): 2832-2839.
[6]	常哲, 王佳鑫, 陆熹, 傅尧. 镍促进电化学还原交叉偶联合成偕二氟烯烃[J]. 有机化学, 2022, 42(1): 147-159.
[7]	李志清, 邱潇杨, 娄江, 王强. 可见光催化偕二氟烯烃碳-氟键官能化反应的研究进展[J]. 有机化学, 2021, 41(11): 4192-4207.
[8]	陈锦杨, 李玉涵, 梅兰, 吴红谕. 新型光敏剂2, 4, 5, 6-四(9-咔唑基)间苯二腈在无金属有机光合成中的应用[J]. 有机化学, 2019, 39(11): 3040-3050.