Ruthenium Catalyzed Selective Acceptorless Dehydrogenation of Allylic Alcohols to α,β-Unsaturated Carbonyls

doi:10.6023/cjoc202107037

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4361-4369.DOI: 10.6023/cjoc202107037 Previous Articles Next Articles

Special Issue: 热点论文虚拟合集

ARTICLES

钌选择性催化烯丙醇无受体脱氢合成α,β-不饱和羰基化合物

刘嘉豪^a, 张世冬^a, 栾自鸿^a, 刘艳^b, 柯卓锋^a^,^*()

a 中山大学材料科学与工程学院聚合物复合材料及功能材料教育部重点实验室广州 510006
b 广东工业大学轻工化工学院广州 510006

收稿日期:2021-07-16 修回日期:2021-08-15 发布日期:2021-08-24
通讯作者: 柯卓锋
作者简介:
† 共同第一作者.
基金资助:
国家自然科学基金(21973113); 国家自然科学基金(21977019); 广东省自然科学杰出青年基金(2015A030306027)

Ruthenium Catalyzed Selective Acceptorless Dehydrogenation of Allylic Alcohols to α,β-Unsaturated Carbonyls

Jiahao Liu^a, Shidong Zhang^a, Zihong Luan^a, Yan Liu^b, Zhuofeng Ke^a()

a Key Laboratory for Polymeric Composite & Functional Materials of Ministry of Education, School of Materials Science and Engineering, Sun Yat-sen University, Guangzhou 510006
b School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006

Received:2021-07-16 Revised:2021-08-15 Published:2021-08-24
Contact: Zhuofeng Ke
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21973113); National Natural Science Foundation of China(21977019); Guangdong Natural Science Funds for Distinguished Young Scholar(2015A030306027)

1. .pdf(2286KB)

Abstract

Transition metal-catalyzed allyllic alcohol selective dehydrogenation to generate the corresponding α,β-unsaturated carbonyl compound has attached great attention. However, most of these methods require stoichiometric quantities of oxidants, which will bring a lot of by-products and lack of atomic economy. Herein, a simple [RuCl₂(p-cymene)]₂ catalyzed system to efficiently catalyze the selective dehydrogenation of allyl alcohol to form α,β-unsaturated carbonyls without the use of additional oxidants or H₂ acceptors has been developed.

Key words: ruthenium, acceptorless dehydrogenation, allylic alcohols, α,β-unsaturated carbonyls

Cite this article

Jiahao Liu, Shidong Zhang, Zihong Luan, Yan Liu, Zhuofeng Ke. Ruthenium Catalyzed Selective Acceptorless Dehydrogenation of Allylic Alcohols to α,β-Unsaturated Carbonyls[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4361-4369.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 7

References 46

[1]	(a) Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681. doi: 10.1021/cr900202j pmid: 19938813
	(b) Choi, J.; MacArthur, A. H. R.; Brookhart, M.; Goldman, A. S. Chem. Rev. 2011, 111, 1761. doi: 10.1021/cr1003503 pmid: 19938813
	(c) Kumar, A.; Bhatti, T. M.; Goldman, A. S. Chem. Rev. 2017, 117, 12357. doi: 10.1021/acs.chemrev.7b00247 pmid: 19938813
[2]	(a) van der Drift, R. C.; Bouwman, E.; Drent, E. J. Organomet. Chem. 2002, 650, 1. doi: 10.1016/S0022-328X(02)01150-6 pmid: 22214981
	(b) Uma, R.; Crévisy, C.; Grée, R. Chem. Rev. 2003, 103, 27. doi: 10.1021/cr0103165 pmid: 22214981
	(c) Cadierno, V.; Crochet, P.; Gimeno, J. Synlett 2008, 1105. pmid: 22214981
	(d) Mantilli, L.; Mazet, C. Chem. Lett. 2011, 40, 341. doi: 10.1246/cl.2011.341 pmid: 22214981
	(e) Ahlsten, N.; Bartoszewicz, A.; Martín-Matute, B. Dalton Trans. 2012, 41, 1660. doi: 10.1039/c1dt11678a pmid: 22214981
[3]	(a) Nakano, T.; Ishii, Y.; Ogawa, M. J. Org. Chem. 1987, 52, 4855. doi: 10.1021/jo00231a006 pmid: 22337651
	(b) Adam, W.; Gelalcha, F. G.; Saha-Möller, C. R.; Stegmann, V. R. J. Org. Chem. 2000, 65, 1915. pmid: 22337651
	(c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620. pmid: 22337651
	(d) Johnston, E. V.; Verho, O.; Kärkäs, M. D.; Shakeri, M.; Tai, C.-W.; Palmgren, P.; Eriksson, K.; Oscarsson, S.; Bäckvall, J.-E. Chem.-Eur. J. 2012, 18, 12202. doi: 10.1002/chem.201202157 pmid: 22337651
	(e) Hill-Cousins, J. T.; Kuleshova, J.; Green, R. A.; Birkin, P. R.; Pletcher, D.; Underwood, T. J.; Leach, S. G.; Brown, R. C. D. ChemSusChem 2012, 5, 326. doi: 10.1002/cssc.201100601 pmid: 22337651
	(f) Nishii, T.; Ouchi, T.; Matsuda, A.; Matsubara, Y.; Haraguchi, Y.; Kawano, T.; Kaku, H.; Horikawa, M.; Tsunoda, T. Tetrahedron Lett. 2012, 53, 5880. doi: 10.1016/j.tetlet.2012.08.095 pmid: 22337651
	(g) Xing, Y.; Li, C.; Meng, J.; Zhang, Z.; Wang, X.; Wang, Z.; Ye, Y.; Sun, K. Adv. Synth. Catal. 2021, 363, 3913. doi: 10.1002/adsc.v363.16 pmid: 22337651
	(h) Mancuso, A. J.; Swern, D. Synthesis 1981, 1981, 165. doi: 10.1055/s-1981-29377 pmid: 22337651
[4]	(a) Wang, G. Z.; Bäckvall, J.-E. J. Chem. Soc., Chem. Commun. 1992, 337. pmid: 12868920
	(b) Almeida, M. L. S.; Beller, M.; Wang, G.-Z.; Bäckvall, J.-E.; Chem.-Eur. J. 1996, 2, 1533. doi: 10.1002/(ISSN)1521-3765 pmid: 12868920
	(c) Almeida, M. L. S.; Kočovský, P.; Bäckvall, J.-E. J. Org. Chem. 1996, 61, 6587. pmid: 12868920
	(d) Nishibayashi, Y.; Yamauchi, A.; Onodera, G.; Uemura, S. J. Org. Chem. 2003, 68, 5875. pmid: 12868920
	(e) Gauthier, S.; Scopelliti, R.; Severin, K. Organometallics 2004, 23, 3769. doi: 10.1021/om049671m pmid: 12868920
	(f) Yi, C. S.; Zeczycki, T. N.; Guzei, I. A. Organometallics 2006, 25, 1047. doi: 10.1021/om0510674 pmid: 12868920
	(g) Nielsen, M.; Kammer, A.; Cozzula, D.; Junge, H.; Gladiali, S.; Beller, M. Angew. Chem., Int. Ed. 2011, 50, 9593. doi: 10.1002/anie.201104722 pmid: 12868920
	(h) Chelucci, G.; Baldino, S.; Baratta, W. Coord. Chem. Rev. 2015, 300, 29. doi: 10.1016/j.ccr.2015.04.007 pmid: 12868920
	(i) Zhang, W.; Meng, C.; Liu, Y.; Tang, Y.; Li, F. Adv. Synth. Catal. 2018, 360, 3751. doi: 10.1002/adsc.v360.19 pmid: 12868920
	(j) Udvardy, A.; Joó, F.; Kathó, Á. Coord. Chem. Rev. 2021, 438, 213871. doi: 10.1016/j.ccr.2021.213871 pmid: 12868920
	(k) Zeng, M.; Song, C.; Cui, D. Chin. J. Org. Chem. 2017, 37, 1352. (in Chinese) doi: 10.6023/cjoc201701027 pmid: 12868920
	(曾明, 宋婵, 崔冬梅, 有机化学, 2017, 37, 1352.) doi: 10.6023/cjoc201701027 pmid: 12868920
[5]	(a) Coleman, M. G.; Brown, A. N.; Bolton, B. A.; Guan, H. Adv. Synth. Catal. 2010, 352, 967. doi: 10.1002/adsc.200900896
	(b) Chakraborty, S.; Lagaditis, P. O.; Förster, M.; Bielinski, E. A.; Hazari, N.; Holthausen, M. C.; Jones, W. D.; Schneider, S. ACS Catal. 2014, 4, 3994. doi: 10.1021/cs5009656
	(c) Budweg, S.; Wei, Z.; Jiao, H.; Junge, K.; Beller, M. ChemSusChem 2019, 12, 2988. doi: 10.1002/cssc.v12.13
	(d) Chun, S.; Ahn, J.; Putta, R. R.; Lee, S. B.; Oh, D.-C.; Hong, S. J. Org. Chem. 2020, 85, 15314. doi: 10.1021/acs.joc.0c02145
	(e) Budweg, S.; Junge, K.; Beller, M. Catal. Sci. Technol. 2020, 10, 3825. doi: 10.1039/D0CY00699H
[6]	(a) Suzuki, T.; Morita, K.; Tsuchida, M.; Hiroi, K. J. Org. Chem. 2003, 68, 1601. doi: 10.1021/jo0262560
	(b) Hanasaka, F.; Fujita, K.; Yamaguchi, R. Organometallics 2004, 23, 1490. doi: 10.1021/om049918f
	(c) Hanasaka, F.; Fujita, K.; Yamaguchi, R. Organometallics 2005, 24, 3422. doi: 10.1021/om0503545
	(d) Hanasaka, F.; Fujita, K.; Yamaguchi, R. Organometallics 2006, 25, 4643. doi: 10.1021/om060475k
	(e) Fujita, K.; Yoshida, T.; Imori, Y.; Yamaguchi, R. Org. Lett. 2011, 13, 2278. doi: 10.1021/ol2005424
	(f) Musa, S.; Shaposhnikov, I.; Cohen, S.; Gelman, D. Angew. Chem., Int. Ed. 2011, 50, 3533. doi: 10.1002/anie.201007367
	(g) Polukeev, A. V.; Petrovskii, P. V.; Peregudov, A. S.; Ezernitskaya, M. G.; Koridze, A. A. Organometallics 2013, 32, 1000. doi: 10.1021/om300921q
	(h) Shi, Y.; Suguri, T.; Kojima, S.; Yamamoto, Y. J. Organomet. Chem. 2015, 799-800, 7.
	(i) Polukeev, A. V.; Wendt, O. F. Organometallics 2017, 36, 639. doi: 10.1021/acs.organomet.6b00846
[7]	(a) Join, B.; Möller, K.; Ziebart, C.; Schröder, K.; Gördes, D.; Thurow, K.; Spannenberg, A.; Junge, K.; Beller, M. Adv. Synth. Catal. 2011, 353, 3023. doi: 10.1002/adsc.v353.16
	(b) Könning, D.; Olbrisch, T.; Sypaseuth, F. D.; Tzschucke, C. C.; Christmann, M. Chem. Commun. 2014, 50, 5014. doi: 10.1039/C4CC01305K
[8]	(a) Oppenauer, R. V. Recl. Trav. Chim. Pays-Bas 1937, 56, 137. doi: 10.1002/recl.v56:2
	(b) de Graauw, C. F.; Peters, J. A.; van Bekkum, H.; Huskens, J. Synthesis 1994, 1007.
	(c) Gunanathan, C.; Milstein, D. Science 2013, 341, 1229712. doi: 10.1126/science.1229712
	(d) Song, H.; Kang, B.; Hong, S. H. ACS Catal. 2014, 4, 2889. doi: 10.1021/cs5007316
	(e) Huang, F.; Liu, Z.; Yu, Z. Angew. Chem., Int. Ed. 2016, 55, 862. doi: 10.1002/anie.201507521
	(f) Kallmeier, F.; Kempe, R. Angew. Chem., Int. Ed. 2018, 57, 46. doi: 10.1002/anie.201709010
	(g) Huang, M.; Liu, J.; Li, Y.; Lan, X.-B.; Su, P.; Zhao, C.; Ke, Z. Catal. Today 2020.
[9]	(a) Dobson, A.; Robinson, S. D. Inorg. Chem. 1977, 16, 137. doi: 10.1021/ic50167a029 pmid: 28051854
	(b) Hamid, M. H. S. A.; Slatford, P. A.; Williams, J. M. J. Adv. Synth. Catal. 2007, 349, 1555. doi: 10.1002/(ISSN)1615-4169 pmid: 28051854
	(c) Watson, A. J. A.; Williams, J. M. J. Science 2010, 329, 635. doi: 10.1126/science.1191843 pmid: 28051854
	(d) Guillena, G.; Ramon, D. J.; Yus, M. Chem. Rev. 2010, 110, 1611. doi: 10.1021/cr9002159 pmid: 28051854
	(e) Johnson, T. C.; Morris, D. J.; Wills, M. Chem. Soc. Rev. 2010, 39, 81. doi: 10.1039/b904495g pmid: 28051854
	(f) Trincado, M.; Banerjee, D.; Grützmacher, H. Energy Environ. Sci. 2014, 7, 2464. doi: 10.1039/C4EE00389F pmid: 28051854
	(g) Kim, S. W.; Zhang, W.; Krische, M. J. Acc. Chem. Res. 2017, 50, 2371. doi: 10.1021/acs.accounts.7b00308 pmid: 28051854
	(h) Chelucci, G. Coord. Chem. Rev. 2017, 331, 1. doi: 10.1016/j.ccr.2016.10.002 pmid: 28051854
	(i) Crabtree, R. H. Chem. Rev. 2017, 117, 9228. doi: 10.1021/acs.chemrev.6b00556 pmid: 28051854
	(j) Corma, A.; Navas, J.; Sabater, M. J. Chem. Rev. 2018, 118, 1410. doi: 10.1021/acs.chemrev.7b00340 pmid: 28051854
	(k) Hu, B.; Zhang, Y.; Yin, G.; Chen, D. Chin. J. Org. Chem. 2020, 40, 53. (in Chinese) doi: 10.6023/cjoc201908017 pmid: 28051854
	(胡博文, 张宇哲, 尹鸽平, 陈大发, 有机化学, 2020, 40, 53.) doi: 10.6023/cjoc201908017 pmid: 28051854
	(l) Wang, C.; Xiao, J. Chin. J. Org. Chem. 2020, 40, 2182. (in Chinese) doi: 10.6023/cjoc202000045 pmid: 28051854
	(王超, 肖建良, 有机化学, 2020, 40, 2182.) doi: 10.6023/cjoc202000045 pmid: 28051854
	(m) Hao, Z.; Liu, K.; Feng, Q.; Dong, Q.; Ma, D.; Han, Z.; Lu, G.-L.; Lin, J. Chin. J. Chem. 2021, 39, 121. doi: 10.1002/cjoc.v39.1 pmid: 28051854
[10]	(a) Choi, J. H.; Kim, N.; Shin, Y. J.; Park, J. H.; Park, J. Tetrahedron Lett. 2004, 45, 4607. doi: 10.1016/j.tetlet.2004.04.113
	(b) Kim, W.-H.; Park, I. S.; Park, J. Org. Lett. 2006, 8, 2543. doi: 10.1021/ol060750z
	(c) Mitsudome, T.; Mikami, Y.; Funai, H.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Angew. Chem., Int. Ed. 2008, 47, 138. doi: 10.1002/(ISSN)1521-3773
	(d) Mitsudome, T.; Mikami, Y.; Ebata, K.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Chem. Commun. 2008, 4804.
	(e) Shimizu, K.; Sugino, K.; Sawabe, K.; Satsuma, A. Chem.-Eur. J. 2009, 15, 2341. doi: 10.1002/chem.v15:10
	(f) Fang, W.; Chen, J.; Zhang, Q.; Deng, W.; Wang, Y. Chem.-Eur. J. 2011, 17, 1247. doi: 10.1002/chem.v17.4
	(g) Marella, R. K.; Prasad Neeli, C. K.; Rao Kamaraju, S. R.; Burri, D. R. Catal. Sci. Technol. 2012, 2, 1833. doi: 10.1039/c2cy20222k
	(h) Shimizu, K.; Kon, K.; Seto, M.; Shimura, K.; Yamazaki, H.; Kondo, J. N. Green Chem. 2013, 15, 418. doi: 10.1039/C2GC36555C
	(i) Shimizu, K.; Kon, K.; Shimura, K.; Hakim, S. S. M. A. J. Catal. 2013, 300, 242. doi: 10.1016/j.jcat.2013.01.005
	(j) Kon, K.; Hakim Siddiki, S. M. A.; Shimizu, K. J. Catal. 2013, 304, 63. doi: 10.1016/j.jcat.2013.04.003
	(k) Yi, J.; Miller, J. T.; Zemlyanov, D. Y.; Zhang, R.; Dietrich, P. J.; Ribeiro, F. H.; Suslov, S.; Abu-Omar, M. M. Angew. Chem., Int. Ed. 2014, 53, 833. doi: 10.1002/anie.201307665
	(l) Chen, J.; Fang, W.; Zhang, Q.; Deng, W.; Wang, Y. Chem. Asian J. 2014, 9, 2187. doi: 10.1002/asia.v9.8
	(m) González Miera, G.; Martínez-Castro, E.; Martín-Matute, B. Organometallics 2018, 37, 636. doi: 10.1021/acs.organomet.7b00220
[11]	Ren, K.; Hu, B.; Zhao, M.; Tu, Y.; Xie, X.; Zhang, Z. J. Org. Chem. 2014, 79, 2170. doi: 10.1021/jo500042h
[12]	(a) Tseng, K.-N. T.; Kampf, J. W.; Szymczak, N. K. ACS Catal. 2015, 5, 5468. doi: 10.1021/acscatal.5b00952
	(b) Hou, C.; Zhang, Z.; Zhao, C.; Ke, Z. Inorg. Chem. 2016, 55, 6539. doi: 10.1021/acs.inorgchem.6b00723
	(c) Wang, Q.; Chai, H.; Yu, Z. Organometallics 2017, 36, 3638. doi: 10.1021/acs.organomet.7b00587
[13]	(a) Soai, K.; Yokoyama, S.; Mochida, K. Synthesis 1987, 1987, 647. doi: 10.1055/s-1987-28035
	(b) Håkansson, A. E.; Palmelund, A.; Holm, H.; Madsen, R. Chem.- Eur. J. 2006, 12, 3243. doi: 10.1002/(ISSN)1521-3765
[14]	Zhu, Y.; Colomer, I.; Donohoe, T. J. Chem. Commun. 2019, 55, 10316. doi: 10.1039/C9CC04383G
[15]	Krätzschmar, F.; Kaßel, M.; Delony, D.; Breder, A. Chem.-Eur. J. 2015, 21, 7030. doi: 10.1002/chem.201406290 pmid: 25808950
[16]	Papa Spadafora, B.; Moreira Ribeiro, F. W.; Matsushima, J. E.; Ariga, E. M.; Omari, I.; Soares, P. M. A.; de Oliveira-Silva, D.; Vinhato, E.; McIndoe, J. S.; Carita Correra, T.; Rodrigues, A. Org. Biomol. Chem. 2021, 19, 5595. doi: 10.1039/d1ob00670c pmid: 34096563
[17]	Hu, D. X.; Shibuya, G. M.; Burns, N. Z. J. Am. Chem. Soc. 2013, 135, 12960. doi: 10.1021/ja4083182
[18]	Talwar, D.; Wu, X.; Saidi, O.; Salguero, N. P.; Xiao, J. Chem.-Eur. J. 2014, 20, 12835. doi: 10.1002/chem.201403701
[19]	Cignarella, G.; Occelli, E.; Testa, E. J. Med. Chem. 1965, 8, 326. doi: 10.1021/jm00327a010
[20]	Tomita, R.; Mantani, K.; Hamasaki, A.; Ishida, T.; Tokunaga, M. Chem.-Eur. J. 2014, 20, 9914. doi: 10.1002/chem.201403373 pmid: 24957504
[21]	Balcells, S.; Haughey, M. B.; Walker, J. C. L.; Josa-Culleré, L.; Towers, C.; Donohoe, T. J. Org. Lett. 2018, 20, 3583. doi: 10.1021/acs.orglett.8b01370 pmid: 29863350
[22]	Li, H.; Chen, H.; Zhou, Y.; Huang, J.; Yi, J.; Zhao, H.; Wang, W.; Jing, L. Chem. Asian J. 2020, 15, 555. doi: 10.1002/asia.v15.5
[23]	Wang, R.; Tang, Y.; Xu, M.; Meng, C.; Li, F. J. Org. Chem. 2018, 83, 2274. doi: 10.1021/acs.joc.7b03174
[24]	Li, C.; Chen, H.; Li, J.; Li, M.; Liao, J.; Wu, W.; Jiang, H. Adv. Synth. Catal. 2018, 360, 1600. doi: 10.1002/adsc.v360.8
[25]	Meiß, R.; Kumar, K.; Waldmann, H. Chem.-Eur. J. 2015, 21, 13526. doi: 10.1002/chem.201502843
[26]	Yang, Y.; Jiang, J.; Qimei, L.; Yan, X.; Zhao, J.; Yuan, H.; Qin, Z.; Wang, M. Molecules 2010, 15, 7075. doi: 10.3390/molecules15107075 pmid: 20944522
[27]	Morrill, C.; Grubbs, R. H. J. Am. Chem. Soc. 2005, 127, 2842. doi: 10.1021/ja044054a
[28]	Kim, D. E.; Kwak, J.; Kim, I. S.; Jeong, N. Adv. Synth. Catal. 2009, 351, 97. doi: 10.1002/adsc.200800657
[29]	Liu, J.; Zhu, J.; Jiang, H.; Wang, W.; Li, J. Chem. Commun. 2010, 46, 415. doi: 10.1039/B922351G
[30]	Susanto, W.; Chu, C.-Y.; Ang, W. J.; Chou, T.-C.; Lo, L.-C.; Lam, Y. J. Org. Chem. 2012, 77, 2729. doi: 10.1021/jo202482h pmid: 22372634
[31]	Zhang, Z.; Wang, Q.; Chen, C.; Han, Z.; Dong, X.-Q.; Zhang, X. Org. Lett. 2016, 18, 3290. doi: 10.1021/acs.orglett.6b01605
[32]	Chen, X.; Zhang, Y.; Wan, H.; Wang, W.; Zhang, S. Chem. Commun. 2016, 52, 3532. doi: 10.1039/C5CC10093C
[33]	Ahmed, M.; Brand, H. E. A.; Peterson, V. K.; Clegg, J. K.; Kepert, C. J.; Price, J. R.; Powell, B. J.; Neville, S. M. Dalton Trans. 2021, 50, 1434. doi: 10.1039/D0DT04007J
[34]	Chavhan, S. W.; Cook, M. J. Chem.-Eur. J. 2014, 20, 4891. doi: 10.1002/chem.201400104 pmid: 24677380
[35]	Zhang, X.-W.; Jiang, G.-Q.; Lei, S.-H.; Shan, X.-H.; Qu, J.-P.; Kang, Y.-B. Org. Lett. 2021, 23, 1611. doi: 10.1021/acs.orglett.1c00043
[36]	An, X.-L.; Chen, J.-R.; Li, C.-F.; Zhang, F.-G.; Zou, Y.-Q.; Guo, Y.-C.; Xiao, W.-J. Chem. Asian J. 2010, 5, 2258. doi: 10.1002/asia.201000315
[37]	Guo, S.-H.; Xing, S.-Z.; Mao, S.; Gao, Y.-R.; Chen, W.-L.; Wang, Y.-Q. Tetrahedron Lett. 2014, 55, 6718. doi: 10.1016/j.tetlet.2014.10.019
[38]	Zhang, G.; Han, X.; Luan, Y.; Wang, Y.; Wen, X.; Ding, C. Chem. Commun. 2013, 49, 7908. doi: 10.1039/c3cc44122a
[39]	You, S.; Zhang, R.; Cai, M. Synthesis 2021, 53, 1962. doi: 10.1055/s-0040-1706621
[40]	Yu, C.-W.; Chen, G. S.; Huang, C.-W.; Chern, J.-W. Org. Lett. 2012, 14, 3688. doi: 10.1021/ol301523q
[41]	Tigineh, G. T.; Liu, L.-K. J. Chin. Chem. Soc. 2019, 66, 1729. doi: 10.1002/jccs.v66.12
[42]	Yu, B.; Zhao, Y.; Zhang, H.; Xu, J.; Hao, L.; Gao, X.; Liu, Z. Chem. Commun. 2014, 50, 2330. doi: 10.1039/c3cc49365b
[43]	Chen, X.-Y.; Sorensen, E. J. J. Am. Chem. Soc. 2018, 140, 2789. doi: 10.1021/jacs.8b00048
[44]	Shen, D.; Miao, C.; Wang, S.; Xia, C.; Sun, W. Org. Lett. 2014, 16, 1108. doi: 10.1021/ol4037083
[45]	Konishi, H.; Kumon, M.; Yamaguchi, M.; Manabe, K. Tetrahedron 2020, 76, 131639. doi: 10.1016/j.tet.2020.131639
[46]	Troxler, F.; Harnisch, A.; Bormann, G.; Seemann, F.; Szabo, L. Helv. Chim. Acta 1968, 51, 1616. doi: 10.1002/hlca.19680510717

钌选择性催化烯丙醇无受体脱氢合成α,β-不饱和羰基化合物

Ruthenium Catalyzed Selective Acceptorless Dehydrogenation of Allylic Alcohols to α,β-Unsaturated Carbonyls

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 7

References 46

Related Articles 15

Recommended Articles

Metrics

Comments

Entry	Additive	Solvent	T/℃	t/h	Yield^b/%
1	—	t-AmOH	100	24	Trace
2^c	Cu(OAc)₂•H₂O	t-AmOH	100	16	93
3^d	Cu(OAc)₂•H₂O	t-AmOH	100	16	93
4	Cu(OAc)₂•H₂O	t-AmOH	100	16	93
5^e	Cu(OAc)₂•H₂O	t-AmOH	100	36	71
6	Cu(OAc)₂•H₂O	t-AmOH	80	36	91
7	Cu(OAc)₂•H₂O	t-AmOH	60	48	Trace
8	Cu(OAc)₂•H₂O	t-AmOH	r.t.	72	Trace
9	AgOAc	t-AmOH	100	16	14^f
10	KOAc	t-AmOH	100	48	85
11	NaOAc	t-AmOH	100	36	72
12	Na₂CO₃	t-AmOH	100	16	76
13	Cu(OTf)₂	t-AmOH	100	84	58
14	Cu(OAc)₂•H₂O	Toluene	100	84	68
15	Cu(OAc)₂•H₂O	EtOH	80	48	Trace
16	Cu(OAc)₂•H₂O	H₂O	100	48	Trace

Entry	Substrate	Product	Yield^b/%
1			93
2			93
3			94
4			91
5			93
6			93
7			94
8			95
9			92
Entry	Substrate	Product	Yield^b/%
10			93
11			90
12			94
13			93
14			92
15			90

[1]	Yan Tian, Rui Dong, Peng Nie, Bo Xu. Synthesis and Characterization of Ruthenium Germyl Complexes with Various Substituents [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 173-179.
[2]	Yue Zhu, Lu Chen, Jing Zhao, Qingrong Sun, Weiqing Yang, Haiyan Fu, Menglin Ma. Synthesis of Quinoline Derivatives by Friedländer Reaction Catalyzed by Ruthenium Complexes of Substituted 8-Hydroxyquinoline [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2528-2542.
[3]	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.
[4]	Mei Wang, Huihua Gong, Haiyan Fu, Xueli Zheng, Hua Chen, Ruixiang Li. Ruthenium Complex-Catalyzed Tandem Reactions of Alcohols with Acetonitriles for Synthesis of α-Substituted Amides [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2418-2427.
[5]	Zengjin Dai, Xumu Zhang, Qin Yin. Advances on Asymmetric Reductive Amination with Ammonium Salts as Amine Sources [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2261-2274.
[6]	Tao Li, Yi Liu, Xue Bai, Zunjun Zhou, Peng Zuo, Miaofeng Ma, Chong-Min Zhong, Ya-Jie Zuo. Preparation of Imidazolium Ion Functionalized HG-II Chiral Ruthenium Catalysts and Their Catalytic Performance in Asymmetric Olefin Metathesis [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1713-1721.
[7]	Xiaolong Fang, Bin Li, Jie Jin, Ning Duan. Homogeneous Catalytic Hydrogenation of Dimethyl Malonate into 1,3-Propanediol [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1407-1413.
[8]	Xinyu Wang, Qihuan Li, Tingbin Wen. Ruthenium-Catalyzed Oxygenative Transformation of Terminal Propargyl Alcohols to Metheyleneketenes via Allenylidene Intermedia-tes: Synthesis ofα,β-Unsaturated Carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 284-296.
[9]	Fang Xiaolong, Duan Ning, Zhang Min, Li Bin. Advances for Ruthenium Catalysts with Metal-Ligand Cooperation for Hydrogenation of Oxalates into Ethylene Glycol [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2692-2701.
[10]	Wang Su, Zhang Youlu, Ba Yanyan, Zhang Jingyu, Sun Demei. Study and Applications of Stereoselective Olefin Metathesis Reactions [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2725-2741.
[11]	Ma Xiantao, Yu Jing, Wang Zilong, Zhang Yun, Zhou Qiuju. Efficient Activation of Allylic Alcohols in Pd-Catalyzed Allylic Substitution Reactions [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2669-2677.
[12]	Lin Cong, Gao Zhenbo, Teng Qiuxun, Xue Bowen, Li Xiaohua, Gao Fei, Shen Liang. Synthesis of Vinyl-Substituted Dihydroisoquinolone via Ru(II)-Catalyzed C—H Functionalization/Annulation of Imidates [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2863-2870.
[13]	Fang Xiaolong, Zhang Min, Duan Ning, Wang Xin, Zhu Hongping. Synthesis and Catalytic Property of New Aminophosphino Ruthenium Carbonyl Complexes [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 226-231.
[14]	Hu Bowen, Zhang Yuzhe, Yin Geping, Chen Dafa. Half-Sandwich Ruthenium(II) Complexes with Bidentate NN Ligands:Active Catalysts for the Synthesis of Quinolines and Pyrroles by Acceptorless Dehydrogenative Cyclization [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 53-60.
[15]	Wang Qiushi, Xie Jianhua, Zhou Qilin. Ruthenium Catalyzed Highly Chemo-and Regio-selective Codimerization of N-Acetyl α-Arylethenamines with Vinylarenes [J]. Chin. J. Org. Chem., 2019, 39(8): 2264-2269.