金催化的环化反应与钯催化的炔醇偶联/环化反应相结合用于合成多取代呋喃衍生物:串联反应的应用范围

doi:10.1016/S1872-2067(15)60994-9

催化学报 ›› 2016, Vol. 37 ›› Issue (2): 288-299.DOI: 10.1016/S1872-2067(15)60994-9

金催化的环化反应与钯催化的炔醇偶联/环化反应相结合用于合成多取代呋喃衍生物:串联反应的应用范围

Chandrasekar Praveen^a, Paramasivan T. Perumal^b

a 中央电化学研究所(科学与工业研究中心实验室)功能材料部, 卡莱科蒂 630003, 印度;
b 中央皮革研究所(科学与工业研究中心实验室)有机化学部, 金奈 600020, 印度

收稿日期:2015-09-09 修回日期:2015-10-12 出版日期:2016-01-30 发布日期:2016-01-31
通讯作者: Chandrasekar Praveen
基金资助:
印度科学技术部.

Extrapolation of the gold-catalyzed cycloisomerization to the palladium-catalyzed cross-coupling/cycloisomerization of acetylenic alcohols for the synthesis of polysubstituted furans: Scope and application to tandem processes

Chandrasekar Praveen^a, Paramasivan T. Perumal^b

a Functional Materials Division, Central Electrochemical Research Institute (CSIR Laboratory), Karaikudi 630003, India;
b Organic Chemistry Division, Central Leather Research Institute (CSIR Laboratory), Adyar, Chennai 600020, India

Received:2015-09-09 Revised:2015-10-12 Online:2016-01-30 Published:2016-01-31
Supported by:
This work was supported by the Department of Science and Technology (INSPIRE Faculty Program), India.

摘要/Abstract

摘要：

开发了一种由金和钯催化π-活化由炔醇合成呋喃衍生物的集成方法. 该合成策略是最显著的特点适用于带环辛基的底物, 其适用范围比之前报道的有很大扩展. 在Sonogashira反应条件下, 由相应底物可直接得到环辛基呋喃. Pd在这些反应中起到2个重要作用: 底物发生偶联反应的关键催化剂; 通过π-活化促进炔醇中间体成环反应. 该方法在一步合成3-碘呋喃反应中作用很突出, 使通过偶联法进一步官能团化成为可能. 我们还将AuBr₃用于多米诺成环/C-H键活化反应和无环前体的成环反应. 本文结果表明, 在该类成环反应中金和钯催化剂相辅相成.

关键词: 呋喃衍生物, 环化反应, 金催化, 钯催化, 一锅法, 串联反应

Abstract:

This paper describes the development of an integrated approach for the preparation of diverse furan derivatives from acetylenic alcohols by gold and palladium catalyzed π-activation chemistry. Notably, this new method was found to be amenable to cyclooctyl-containing substrates, which represents a significant extension to this methodology compared with our previous reports. Furthermore, this newly developed method allowed for the direct construction of cyclooctyl furans from their synthetic precursors under Sonogashira conditions. Experimental results revealed that palladium played two major functions in these reactions, including (1) an essential catalyst in the cross-coupling reaction of the substrates; and (2) facilitating the cyclization of the acetylenic alcohol intermediates through a typical π-activation process. The scope of this chemistry was highlighted by the one-pot synthesis of 3-iodofuran, which provided an opportunity for further functionalization (via coupling methods). Finally, the AuBr₃ protocol was also elaborated to domino cyclization/C-H activation reactions, as well as the cyclization of acyclic precursors. Taken together, the results of this study demonstrate that gold and palladium catalysts can be used to complement each other in cyclization reactions.

Key words: Furan derivatives, Cycloisomerization, Gold catalysis, Palladium catalysis, One-pot operation, Tandem reactions

Chandrasekar Praveen, Paramasivan T. Perumal. 金催化的环化反应与钯催化的炔醇偶联/环化反应相结合用于合成多取代呋喃衍生物:串联反应的应用范围[J]. 催化学报, 2016, 37(2): 288-299.

Chandrasekar Praveen, Paramasivan T. Perumal. Extrapolation of the gold-catalyzed cycloisomerization to the palladium-catalyzed cross-coupling/cycloisomerization of acetylenic alcohols for the synthesis of polysubstituted furans: Scope and application to tandem processes[J]. Chinese Journal of Catalysis, 2016, 37(2): 288-299.

×
扫码分享

导出引用管理器 EndNote|Ris|BibTeX

链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(15)60994-9

https://www.cjcatal.com/CN/Y2016/V37/I2/288

参考文献

[1] C. H. M. Amijs, C. Ferrer, A. M. Echaverren, Chem. Commun., 2007, 698.
[2] A. Hoffmann-Roder, N. Krause, Org. Biomol. Chem., 2005, 3, 387.
[3] A. S. K. Hashmi, Angew. Chem. Int. Ed., 2005, 44, 6990.
[4] A. Arcadi, S. Di Giuseppe, Curr. Org. Chem., 2004, 8, 795.
[5] R. A. Widenhoefer, X. Q. Han, Eur. J. Org. Chem., 2006, 4555.
[6] H. C. Shen, Tetrahedron, 2008, 64, 7847.
[7] Z. G. Li, C. Brouwer, C. He, Chem. Rev., 2008, 108, 3289.
[8] L. M. Zhang, J. W. Sun, S. A. Kozmin, Adv. Synth. Catal., 2006, 348, 2271.
[9] N. Asao, Synlett, 2006, 1645.
[10] S. M. Ma, S. C. Yu, Z. H. Gu, Angew. Chem. Int. Ed., 2006, 45, 200.
[11] A. M. Echavarren, C. Nevado, Chem. Soc. Rev., 2004, 33, 431.
[12] G. Dyker, Angew. Chem. Int. Ed., 2000, 39, 4237.
[13] A. S. K. Hashmi, Gold Bull., 2004, 37, 51.
[14] R. Skouta, C. J. Li, Tetrahedron, 2008, 64, 4917.
[15] N. D. Shapiro, F. D. Toste, Synlett, 2010, 675.
[16] A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. Int. Ed., 2006, 45, 7896.
[17] D. J. Gorin, F. D. Toste, Nature, 2007, 446, 395.
[18] A. S. K. Hashmi, Chem. Rev., 2007, 107, 3180.
[19] A. Fürstner, P. W. Davies, Angew. Chem. Int. Ed., 2007, 46, 3410.
[20] M. Rudolph, A. S. K. Hashmi, Chem. Soc. Rev., 2012, 41, 2448.
[21] A. S. K. Hashmi, M. Rudolph, Chem. Soc. Rev., 2008, 37, 1766.
[22] E. Jiménez-Núñez, A. M. Echavarren, Chem. Commun., 2007, 333.
[23] A. S. K. Hashmi, Gold Bull., 2003, 36, 1.
[24] C. Praveen, P. Kiruthiga, P. T. Perumal, Synlett, 2009, 1990.
[25] C. Praveen, S. Jegatheesan, P. T. Perumal, Synlett, 2009, 2795.
[26] C. Praveen, A. Kalyanasundaram, P. T. Perumal, Synlett, 2010, 777.
[27] C. Praveen, Y. W. Sagayaraj, P. T. Perumal, Tetrahedron Lett., 2009, 50, 644.
[28] C. Praveen, K. Karthikeyan, P. T. Perumal, Tetrahedron, 2009, 65, 9244.
[29] Y. P. Zhu, J. J. Yuan, Y. T. Li, M. Gao, L. P. Cao, J. Y. Ding, A. X. Wu, Synlett, 2011, 52.
[30] C. Praveen, A. Ayyanar, P. T. Perumal, Bioorg. Med. Chem. Lett., 2011, 21, 4170.
[31] H. Gasper, S. Santos, M. Carbone, A. S. Rodrigues, A. I. Rodrigues, M. J. Uriz, S. M. S. Feio, D. Melck, M. Humanes, M. Gavagnin, J. Nat. Prod., 2008, 71, 2049.
[32] H. Hikino, Y. Hikino, I. Yosioka, Chem. Pharm. Bull., 1964, 12, 755.
[33] R. C. Cambie, P. S. Rutledge, X. S. Yang, P. R. Bergquist, J. Nat. Prod., 1998, 61, 1416.
[34] M. Gavagnin, E. Mollo, F. Castelluccio, A. Crispino, G. Cimino, J. Nat. Prod., 2003, 66, 1517.
[35] H. Inouye, H. Matsumara, M. Kawasaski, K. Inoue, M. Tsukada, M. Tabata, Phytochemistry, 1981, 20, 1701.
[36] M. Kobayashi, A. Muroyama, H. Nakamura, J. Kobayashi, Y. Ohizumi, J. Pharmacol. Exp. Ther., 1991, 257, 90.
[37] H. Sakamoto, K. I. Furukawa, K. Matsunaga, H. Nakamura, Y. Ohizumi, Biochemistry, 1995, 34, 12570.
[38] W. L. Xiao, H. J. Zhu, Y. H. Shen, R. T. Li, S. H. Li, H. D. Sun, Y. T. Zheng, R. R. Wang, Y. Lu, C. Wang, Q. T. Zheng, Org. Lett., 2005, 7, 2145.
[39] N. T. Patil, H. Wu, Y. Yamamoto, J. Org. Chem., 2005, 70, 4531.
[40] T. L. Yao, X. X. Zhang, R. C. Larock, J. Am. Chem. Soc., 2004, 126, 11164.
[41] S. Goncalves, A. Wagner, C. Mioskowski, R. Baati, Tetrahedron Lett., 2009, 50, 274.
[42] M. Yoshida, M. Al-Amin, K. Matsuda, K. Shishido, Tetrahedron Lett., 2008, 49, 5021.
[43] J. L. Zhang, H. G. Schmalz, Angew. Chem. Int. Ed., 2006, 45, 6704.
[44] A. S. K. Hashmi, L. Schwarz, J. H. Choi, T. M. Frost, Angew. Chem. Int. Ed., 2000, 39: 2285.
[45] C. H. Oh, V. R. Reddy, A. Kim, C. Y. Rhim, Tetrahedron Lett., 2006, 47, 5307.
[46] G. Mehta, N. S. Likhite, Tetrahedron Lett., 2008, 49, 7113.
[47] H-K Yim, Y. Liao, H. N. C. Wong, Tetrahedron, 2003, 59, 1877.
[48] A. Chakraborty, G. K. Kar, J. K. Ray, Tetrahedron, 1997, 53, 2989.
[49] K. Harada, Y. Tonoi, H. Kato, Y. Fukuyama, Tetrahedron Lett., 2002, 43, 3829.
[50] R. E. Patre, S. Gawas, S. Sen, P. S. Parameswaran, S. G. Tilve, Tetrahedron Lett., 2007, 48, 3517.
[51] J. S. Foot, A. T. Phillis, P. P. Sharp, A. C. Wills, M. G. Banwell, Tetrahedron Lett., 2006, 47, 6817.
[52] G. Blay, L. Cardona, B. Garca, J. R. Pedro, J. J. Snchez, J. Org. Chem., 1996, 61, 3815.
[53] M. Inoue, A. J. Frontier, S. J. Danishefsky, Angew. Chem. Int. Ed., 2000, 39, 761.
[54] M. Yoshida, M. Al-Amin, K. Shishido, Synthesis, 2009, 2454.
[55] A. Blanc, K. Tenbrink, J. M. Weibel, P. Pale, J. Org. Chem., 2009, 74, 5342.
[56] S. Borghèse, B. Louis, A. Blanc, P. Pale, Catal. Sci. Technol., 2011, 1, 981.
[57] C. Praveen, C. Iyyappan, P. T. Perumal, Tetrahedron Lett., 2010, 51, 4767.
[58] C. Praveen, C. Iyyappan, K. Girija, K. S. Kumar, P. T. Perumal, J. Chem. Sci., 2012, 124, 451.
[59] C. Praveen, A. Ayyanar, P. T. Perumal, Bioorg. Med. Chem. Lett., 2011, 21, 4072.
[60] C. Praveen, P. DheenKumar, D. Muralidharan, P. T. Perumal, Bioorg. Med. Chem. Lett., 2010, 20, 7292.
[61] K. Parthasarathy, C. Praveen, C. Balachandran, P. S. Kumar, S. Ignacimuthu, P. T. Perumal, Bioorg. Med. Chem. Lett., 2013, 23, 2708.
[62] K. Parthasarathy, C. Praveen, P. S. Kumar, C. Balachandran, P. T. Perumal, RSC Adv., 2015, 5, 15818.
[63] C. Praveen, S. Narendiran, P. Dheenkumar, P. T. Perumal, J. Chem. Sci., 2013, 125, 1543.
[64] C. R. Johnson, J. P. Adams, M. P. Braun, C. B. W. Senanayake, P. M. Wovkulich, M. R. Uskokovi?, Tetrahedron Lett., 1992, 33, 917.
[65] D. K. Mohapatra, B. Chatterjee, M. K. Gurjar, Tetrahedron Asymmetry, 2008, 19, 1568.
[66] C. K. Sha, S. J. Huang, Z. P. Zhan, J. Org. Chem., 2002, 67, 831.
[67] A. L. Germal, J. L. Luche, J. Am. Chem. Soc., 1981, 103, 5454.
[68] A. Mayasundari, D. G. J. Young, Tetrahedron Lett., 2001, 42, 203.
[69] K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett., 1975, 16, 4467.
[70] R. Chinchilla, C. Nájera, Chem. Rev., 2007, 107, 874.
[71] E. Fillion, R. L. Beingessner, J. Org. Chem., 2003, 68, 9485.
[72] L. A. Paquette, J. Ezquerra, W. He, J. Org. Chem., 1995, 60, 1435.
[73] A. B. Neef, C. Schultz, Angew. Chem. Int. Ed., 2009, 48, 1498.
[74] A. E. Sadak, T. Arslan, N. Celebioglu, N. Saracoglu, Tetrahedron, 2010, 66, 3214.
[75] C. B. Reese, A. Shaw, J. Chem. Soc. Perkin Trans. 1, 1975, 2422.
[76] G. Zeni, R. C. Larock, Chem. Rev., 2006, 106, 4644.
[77] T. W. Lyons, M. S. Sanford, Chem. Rev., 2010, 110, 1147.
[78] A. Bacchi, M. Costa, N. Della Cá, M. Fabbricatore, A. Fazio, B. Gabriele, C. Nasi, G. Salerno, Eur. J. Org. Chem., 2004, 574.
[79] A. Arcadi, S. Cacchi, M. D. Rosario, G. Fabrizi, F. Marinelli, J. Org. Chem., 1996, 61, 9280.
[80] B. Gabriele, G. Salerno, A. Fazio, R. Pittelli, Tetrahedron, 2003, 59, 6251.
[81] P. Peng, B. X. Tang, S. F. Pi, Y. Liang, J. H. Li, J. Org. Chem., 2009, 74, 3569.
[82] R. D. Stephens, C. E. Castro, J. Org. Chem., 1963, 28, 3313.
[83] E. Negishi, Acc. Chem. Res., 1982, 15, 340.
[84] E. Erdik, Tetrahedron, 1992, 48, 9577.
[85] M. Miyaura, A. Suzuki, Chem. Rev., 1995, 95, 2457.
[86] J. K. Stille, Angew. Chem. Int. Ed., 1986, 25, 508.
[87] H. A. Dieck, R. F. Heck, J. Am. Chem. Soc., 1974, 96, 1133.
[88] G. Dyker, E. Muth, A. S. K. Hashmi, L. Ding, Adv. Synth. Catal., 2003, 345, 1247.
[89] M. T. Reetz, K. Sommer, Eur. J. Org. Chem., 2003, 3485.
[90] J. A. Marshal, B. G. Shearer, S. L. Crooks, J. Org. Chem., 1987, 52, 1236.
[91] S. Kulyk, W. G. Dougherty Jr., W. S. Kassel, M. J. Zdilla, S. McN. Sieburth, Org. Lett., 2011, 13, 2180.

金催化的环化反应与钯催化的炔醇偶联/环化反应相结合用于合成多取代呋喃衍生物:串联反应的应用范围

Extrapolation of the gold-catalyzed cycloisomerization to the palladium-catalyzed cross-coupling/cycloisomerization of acetylenic alcohols for the synthesis of polysubstituted furans: Scope and application to tandem processes

PDF

可视化

被引次数

摘要/Abstract

引用本文

使用本文

扫码分享

参考文献

相关文章 15

编辑推荐

Metrics

[1]	刘成, 陈梦宁, 时应章, 王志文, 郭韦, 林森, 毕进红, 吴棱. 超薄ZnTi-LDH纳米片作为一种具有路易斯酸和布朗斯特酸的双功能光催化剂用于串联反应合成N-亚苄基苯胺[J]. 催化学报, 2023, 49(6): 102-112.
[2]	李倩, 刘䶮, 李灿. 钯催化不对称烯丙基化/去对称化反应合成无保护基的2-喹啉酮骨架环状氨基酸[J]. 催化学报, 2023, 47(4): 222-228.
[3]	桂清文, 滕帆, 喻鹏, 吴一帆, 农志彬, 杨龙汐, 陈祥, 阳天宝, 何卫民. 可见光诱导Z型V₂O₅/g-C₃N₄异质结催化未活化烯烃串联反应[J]. 催化学报, 2023, 44(1): 111-116.
[4]	张姜, 王子剑, 陈慕耕, 朱义峰, 刘永梅, 贺鹤勇, 曹勇, 包信和. 氮掺杂碳层包覆纳米金催化5-羟甲基糠醛非临氢转化制5-甲基糠醛[J]. 催化学报, 2022, 43(8): 2212-2222.
[5]	洪峰, 王升扬, 张军营, 付俊红, 蒋齐可, 孙科举, 黄家辉. 金属载体强相互作用增强Au/TiO₂催化剂在3-硝基苯乙烯选择性加氢反应的活性[J]. 催化学报, 2021, 42(9): 1530-1537.
[6]	王凯, 王彬力, 刘相慧, 樊红军, 刘龑, 李灿. 钯催化烯基苯并噁嗪酮基于内球型机理的线性和不对称烯丙基烷基化反应[J]. 催化学报, 2021, 42(7): 1227-1237.
[7]	罗靖洁, 董亚南, Corinne Petit, 梁长海. 不可还原材料负载的纳米金催化剂: 理性设计与优化[J]. 催化学报, 2021, 42(5): 670-693.
[8]	吴凡, 贺雷, 李文翠, 路饶, 王阳, 陆安慧. 氮化硼负载的高分散Au-CuO_x纳米颗粒用于低温CO氧化[J]. 催化学报, 2021, 42(3): 388-395.
[9]	李莹, 呼延成, 季定纬, 何固城, 张炜松, 丛玉凤, 陈庆安. 酸催化1,3-环二酮的选择性C-,O-异戊烯基化反应[J]. 催化学报, 2020, 41(9): 1401-1409.
[10]	邓天宇, 许光月, 傅尧. Cu/SBA-15-SO₃H催化木糖一锅转化制备糠醇[J]. 催化学报, 2020, 41(3): 404-414.
[11]	路饶, 贺雷, 王阳, 高新芊, 李文翠. 镍掺杂对氧化铝纳米片负载金催化剂在CO氧化反应中的促进作用[J]. 催化学报, 2020, 41(2): 350-356.
[12]	李明浩, 吴丰田, 顾彦龙. Brönsted酸性离子液体催化α-羟基丙酮和2-苯基吲哚反应合成苯并[a]咔唑[J]. 催化学报, 2019, 40(8): 1135-1140.
[13]	代兴超, 王斌, 王爱勤, 石峰. Pd/PAL催化二氧化碳、氢气和胺反应合成甲酰胺[J]. 催化学报, 2019, 40(8): 1141-1146.
[14]	张文珍, 孙玉乾, 张敏, 周辉, 吕小兵. 银催化炔基腙与二氧化碳的羧化环化反应[J]. 催化学报, 2019, 40(8): 1153-1159.
[15]	任国庆, 裴广贤, 张景才, 李为臻. CeO₂对抗烧结AuGMgGa₂O₄催化剂用于水汽变换和催化燃烧反应的促进作用[J]. 催化学报, 2019, 40(4): 600-608.