Zirconocene Catalysis in Organoaluminum Synthesis of 1-Alkenyl Sulfones and Sulfides

Abstract

The Cp₂ZrCl₂-catalyzed methylalumination of 1-alkynyl sulfones and 1-alkynyl sulfides with Me₃Al, followed by deuterolysis or hydrolysis, affords the corresponding β,β-disubstituted 1-alkenyl sulfones and 1-alkenyl sulfides in high yields. S-Methyl methanethiosulfonate is shown to be a convenient and efficient sulfanylating agent for 1-alkenylaluminum derivatives.

Key words

alkynyl sulfones - alkynyl sulfides - alkenylaluminums - methylalumination - zirconocene catalysis

• References

• 1 Negishi E. Acc. Chem. Res. 1987; 20: 65
• 2 Ramazanov IR, Kadikova RN, Saitova ZR, Dzhemilev UM. Asian J. Org. Chem. 2015; 4: 1301
• 3 Ramazanov IR, Kadikova RN, Saitova ZR, Nadrshina ZI, Dzhemilev UM. Synlett 2016; 27: 2567
• 4 Van Horn DE, Negishi E.-i. J. Am. Chem. Soc. 1978; 100: 2252
• 5 Nakamura H, Yamamoto H. Patent PCT Int. Appl. WO 2005043630, 2005 ; Chem. Abstr. 2005, 142, 440277
• 6 Guangwei W, Gangguo Z, Negishi E.-i. J. Organomet. Chem. 2007; 692: 4731
• 7 Ma S, Negishi E.-i. J. Org. Chem. 1997; 62: 784
• 8 Xie M, Huang X. Synlett 2003; 477
• 9 Xie M, Liu L, Wang J, Wang S. J. Organomet. Chem. 2005; 690: 4058
• 10 Sklute G, Bolm G, Marek I. Org. Lett. 2007; 9: 1259
• 11 Xie M, Lin G, Zhang J, Li M, Feng C. J. Organomet. Chem. 2010; 695: 882
• 12 Maezaki N, Sawamoto H, Yoshigami R, Suzuki T, Tanaka T. Org. Lett. 2003; 5: 1345
• 13 Maezaki N, Sawamoto H, Suzuki T, Yoshigami R, Tanaka T. J. Org. Chem. 2004; 69: 8387
• 14 Knochel P In Comprehensive Organic Synthesis . Vol. 4. Trost BM, Fleming I, Semmelhack MF. Chap. 4 Pergamon; New York: 1991: 865-911
• 15 Negishi E. Pure Appl. Chem. 1981; 53: 2333
• 16 Negishi E. Bull. Chem. Soc. Jpn. 2007; 80: 233
• 17 Dzhemilev UM, Ibragimov AG, Zolotarev AP. Mendeleev Commun. 1992; 2: 135
• 18 Muslukhov RR, Khalilov LM, Ramazanov IR, Sharipova AZ, Ibragimov AG, Dzhemilev UM. Russ. Chem. Bull. 1997; 46: 2082
• 19 Dzhemilev UM, Ibragimov AG, Gilyazev RR, Khafizova LO. Tetrahedron 2004; 60: 1281
• 20 Brown HC, Ravindran N. Synthesis 1973; 42
• 21 Negishi E, Van Horn DE, Yoshida T. J. Am. Chem. Soc. 1985; 107: 6639
• 22 Ramazanov IR, Kadikova RN, Dzhemilev UM. Zh. Org. Khim. 2013; 49: 335
• 23 Kadikova RN, Ramazanov IR, Zosim TP, Dzhemilev UM. J. Organomet. Chem. 2014; 763–764: 14
• 24 Ramazanov IR, Kadikova RN, Zosim TP, Dzhemilev UM. Synthesis 2015; 47: 2670
• 25 Zakharkin LI, Gavrilenko VV. Bull. Acad. Sci. USSR Div. Chem. Sci. 1960; 9: 1294
• 26 Ibragimov AG, Ramazanov IR, Khalilov LM, Sultanov RM, Dzhemilev UM. Mendeleev Сommun. 1996; 6: 231
• 27 Chemla F, Karoyan P. Org. Synth. Coll. Vol. X . Wiley; New York: 2004: 546
• 28 Kopp F, Sklute G, Polborn K, Marek I, Knochel P. Org. Lett. 2005; 7: 3789
• 29 Gold JB. Ph.D. Dissertation . University of Cambridge; UK: 2008