Synthesis, Inhaltsverzeichnis Synthesis 2022; 54(11): 2687-2695DOI: 10.1055/a-1736-8721 paper Palladium-Catalyzed Semihydrogenation of Alkynes with EtOH: Highly Stereoselective Synthesis of E- and Z-Alkenes Chengniu Wang∗ a Medical School, Institute of Reproductive Medicine, Nantong University, Nantong 226001, Jiangsu, P. R. of China , Jin Dong‡ a Medical School, Institute of Reproductive Medicine, Nantong University, Nantong 226001, Jiangsu, P. R. of China , Tingting Li a Medical School, Institute of Reproductive Medicine, Nantong University, Nantong 226001, Jiangsu, P. R. of China , Xi Zhao a Medical School, Institute of Reproductive Medicine, Nantong University, Nantong 226001, Jiangsu, P. R. of China , Dawei Xu∗ b Department of Orthopaedics, Affiliated Hospital 2 of Nantong University, Nantong 226001, Jiangsu, P. R. of China › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A palladium-catalyzed semihydrogenation of alkynes to E- and Z-alkenes employing EtOH as the hydrogenating agent is reported. The selectivity of the reaction system was effectively controlled by ligand/additive and solvent regulation. The use of sodium acetate/triethanolamine (NaOAc/TEOA), THF, and (1R,2R)-bis[(2-methoxyphenyl)phenylphosphino]ethane [(R,R)-DIPAMP] in CH3CN was critical for the stereoselective semihydrogenation of alkynes. The general applicability of this procedure was highlighted by the synthesis of more than 36 alkenes, in good yields with high stereoselectivities. Keywords Keywordssemihydrogenation - alkynes - palladium-catalyzed - highly stereoselective - EtOH as a hydrogen source Volltext Referenzen References 1a Sano S, Matsumoto T, Yano T, Toguchi M, Nakao M. Synlett 2015; 26: 2135 1b Umezawa T, Seino T, Matsuda F. Org. Lett. 2012; 14: 4206 1c Aggarwal VK, Fulton JR, Sheldon CG, de Vicente J. J. Am. Chem. Soc. 2003; 125: 6034 1d Maercker A. Org. React. 1965; 14: 270 2a Osborn JA, Jardine FH, Young JF, Wilkinson G. J. Chem. Soc. A. 1966; 1711 2b Huang YM, Wu D, Huang JS, Guo Q, Li J, You JS. Angew. Chem. Int. Ed. 2014; 53: 12158 3a Zhang N, Quan ZJ, Zhang Z, Da Y X, Wang XC. Chem. Commun. 2016; 52: 14234 3b Pawar PM, Jarag KJ, Shankarling GS. Green Chem. 2011; 13: 2130 3c Perkin WH. J. Chem. Soc. 1868; 21: 53 3d Dippy JF. J, Evans RM. J. Org. Chem. 1950; 15: 451 4a Baudin JB, Hareau G, Julia SA, Ruel O. Tetrahedron Lett. 1991; 32: 1175 4b Robiette R, Pospíšil J. Eur. J. Org. Chem. 2013; 836 4c Alonso DA, Fuensanta M, Nájera C, Varea M. J. Org. Chem. 2005; 70: 6404 4d Zajc B, Kumar R. Synthesis 2010; 1822 5a Corma A, Iborra S, Velty A. Chem. Rev. 2007; 107: 2411 5b Fouche M, Roone L, Barrett AG. M. J. Org. Chem. 2012; 77: 3060 5c Radkowski K, Sundararaju B, Fürstner A. Angew. Chem. Int. Ed. 2013; 52: 355 5d Srimani D, Diskin-Posner Y, Ben-David Y, Milstein D. Angew. Chem. Int. Ed. 2013; 52: 14131 5e Johnson NB, Lennon IC, Moran PH, Ramsden JA. Acc. Chem. Res. 2007; 40: 1291 5f Tron GC, Pirali T, Sorba G, Pagliai F, Busacca S, Genazzani AA. J. Med. Chem. 2006; 49: 3033 6 Lindlar H, Dubuis R. Org. Synth. 1966; 46: 89 7a Marvell EN. Li T. Synthesis 1973; 457 7b Brunet J, Gallois P, Caubere P. J. Org. Chem. 1980; 45: 1937 7c Choudary BM, Sharma GV. M, Bharathi P. Angew. Chem. Int. Ed. 1989; 28: 465 7d Choi JC, Yoon NM. Tetrahedron Lett. 1996; 37: 1057 7e Alonso F, Osante I, Yus M. Tetrahedron 2007; 63: 93 7f Hauwert P, Maestri G, Sprengers JW, Catellani M, Elsevier CJ. Angew. Chem. Int. Ed. 2008; 47: 3223 7g Haberberger M, Irran E, Enthaler S. Eur. J. Inorg. Chem. 2011; 2797 7h Qi X, Liu X, Qu LB, Liu Q, Lan Y. J. Catal. 2018; 362: 25 8 Yang YF, Wang CN, Sun YF, Man XY, Li JX, Sun F. Chem. Commun. 2019; 55: 1903 9a Liu Y, Hu L, Chen H, Du H. Chem. Eur. J. 2015; 21: 3495 9b Richmond E, Moran J. J. Org. Chem. 2015; 80: 6922 9c Fu S, Chen N, Liu X, Shao Z, Luo S, Liu Q. J. Am. Chem. Soc. 2016; 138: 8588 10a Garbe M, Budweg S, Papa V, wie Z, Hornke H, Bachmann S, Scalone M, Spannenberg A, Jiao H, Junge K, Beller M. Catal. Sci. Technol. 2020; 10: 3994 10b Liu X, Liu B, Liu Q. Angew. Chem. Int. Ed. 2020; 59: 6750 10c Liu J, Wei Z, Yang J, Ge Y, Wei D, Jackstell R, Jiao H, Beller M. ACS Catal. 2020; 10: 12167 10d Tokmic K, Fout AR. J. Am. Chem. Soc. 2016; 138: 13700 11a Hauwert P, Maestri G, Sprengers JW, Catellani M, Elsevier CJ. Angew. Chem. Int. Ed. 2008; 47: 3223 11b Wagh YS, Asao N. J. Org. Chem. 2015; 80: 847 11c Shibahara F, Mizuno T, Shibata Y, Murai T. Bull. Chem. Soc. Jpn. 2020; 93: 332 11d Fan C, Hou J, Chen YJ, Ding KL, Zhou QL. Org. Lett. 2021; 23: 2074 12a Rej S, Madasu M, Tan CS, Hsia CF, Huang MH. Chem. Sci. 2018; 9: 2517 12b Park BY, Lim T, Han MS. Chem. Commun. 2021; 57: 6891 12c Zhou YP, Mo ZB, Luecke MP, Driess M. Chem. Eur. J. 2018; 24: 4780 13 Luo F, Pan CD, Wang WH, Ye ZS, Cheng J. Tetrahedron 2010; 66: 1399 14a Wang YL, Huang ZD, Huang Z. Nat. Catal. 2019; 2: 529 14b Huang ZD, Wang YL, Leng XB, Huang Z. J. Am. Chem. Soc. 2021; 143: 4824 15 Gong DW, Hu BW, Yang WW, Kong DG, Xia HP, Chen DF. Organometallics 2020; 39: 862 16 Wang CN, Gong SN, Liang ZP, Sun YF, Cheng R, Yang BH, Liu YR, Yang YF, Sun F. ACS Omega 2019; 4: 16045 17 Gieshoff TN, Welther A, Kessler MT, Prechtl MH. G, Jacobi von Wangelin A. Chem. Commun. 2014; 50: 2261 18 Sklyaruk J, Zubar V, Borghs JC, Rueping M. Org. Lett. 2020; 22: 6067 19 Petrova J, Kirilov M, Momchilova S, Kossev K. Phosphorus Surfur 1988; 40: 69 20 Hwang JJ, Lin RL, Shieh RL, Jwo JJ. J. Mol. Catal. A: Chem. 1999; 142: 125 21 Tai CC, Yu MS, Chen YL, Chuang WH, Lin TH, Yap GP. A, Ong TG. Chem. Commun. 2014; 50: 4344 22 Das M, O’Shea DF. Org. Lett. 2016; 18: 336 23 Paul SC, Mizuno S, Lee HJ, Zheng X, Chajkowisk S, Rimoldi JM, Conney A, Suh N, Rimando AM. Eur. J. Med. Chem. 2010; 45: 3702 24 Tseng CC, Li M, Mo B, Warren SA, Spivey AC. Chem. Lett. 2011; 40: 995 25 Giorgio C, Susanna F. J. Mol. Catal. A: Chem. 2014; 393: 191 26 Landge VG, Yadav V, Subramanian M, Dangarh P, Balaraman E. Chem. Commun. 2019; 55: 6130 27 Derman SC, Schwan AL. J. Org. Chem. 2012; 77: 10978 28 Yu L, Huang Y, Wei Z, Ding Y, Su C, Xu Q. J. Org. Chem. 2015; 80: 8677 29 Li Y, Luo X, Chen X, Chen L, Zhang K. Chem. Commun. 2019; 55: 2170 30 Shi H, Dai SW, Wang B, Cao S. Organometallics 2018; 37: 459 31 Zhang B, Feng P, Cui Y, Jiao N. Chem. Commun. 2012; 48: 7280 32 Yao CZ, Li QQ, Wang MM, Ning XS, Kang YB. Chem. Commun. 2015; 51: 7729 33 Amani J, Sodagar E, Molander GA. Org. Lett. 2016; 18: 732 Zusatzmaterial Zusatzmaterial Supporting Information
