Synthesis 2017; 49(19): 4523-4534
DOI: 10.1055/s-0036-1589062
paper
© Georg Thieme Verlag Stuttgart · New York

Zirconium-Catalyzed Alkyne Carbo- and Cycloalumination Reactions in Stereoselective Preparation of 1-Alkenyl Selenides

Rita N. Kadikova*
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   Email: kadikritan@gmail.com
,
Ilfir R. Ramazanov
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   Email: kadikritan@gmail.com
,
Alexey V. Vyatkin
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   Email: kadikritan@gmail.com
,
Usein M. Dzhemilev
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   Email: kadikritan@gmail.com
› Author Affiliations
This work was supported by the Russian Foundation for Basic Research (Grant No. 16-33-60167 and 16-33-00403), which are gratefully acknowledged.
Further Information

Publication History

Received: 19 May 2017

Accepted after revision: 25 May 2017

Publication Date:
20 July 2017 (online)


Abstract

The Cp2ZrCl2-catalyzed methylalumination and сycloalumination of 1-alkynyl selenides followed by deuterolysis or hydrolysis affords corresponding (Z)-1-alkenyl selenides in high yields. Alternatively, (E)-1-alkenyl selenides were prepared by the reaction of 1-alkenylaluminums with organic diselenides in a one-pot procedure starting from the corresponding 1-alkynes, which provides a versatile tool for the preparation of stereo-defined unsaturated organic derivatives of selenium.

Supporting Information

 
  • References

  • 1 Palomba M. Bagnoli L. Marin F. Santi C. Sancineto L. Phosphorus, Sulfur Silicon Relat. Elem. 2016; 191: 235
  • 2 Mugesh G. du Mont W. Sies H. Chem. Rev. 2001; 101: 2125
  • 3 Nogueira CW. Zeni G. Rocha JB. T. Chem. Rev. 2004; 104: 6255
  • 4 Perin G. Lenardão EJ. Jacob RG. Panatieri RB. Chem. Rev. 2009; 109: 1277
  • 5 Beletskaya IP. Ananikov VP. Chem. Rev. 2011; 111: 1596
  • 6 Beletskaya IP. Ananikov VP. Eur. J. Org. Chem. 2007; 3431
  • 7 Orlov NV. ChemistryOpen 2015; 4: 682
  • 8 Ferreira JT. B. Comasseto JV. J. Organomet. Chem. 1981; 216: 287
  • 9 Gosselck J. Angew. Chem., Int. Ed. Engl. 1963; 2: 660
  • 10 Sharpless KB. Lauer RF. J. Am. Chem. Soc. 1973; 95: 2697
  • 11 Miyashita M. Suzuki T. Hoshino M. Yoshikoshi A. Tetrahedron 1997; 53: 12469
  • 12 Barros OS. R. Lang ES. Oliveira CA. F. Peppe C. Zeni G. Tetrahedron Lett. 2002; 43: 7921
  • 13 Peppe C. Lang ES. Ledesma GN. de Castro LB. do Rego Barros OS. de Azevedo Mello P. Synlett 2005; 3091
  • 14 Zeni G. Stracke MP. Nogueira CW. Braga AL. Menezes PH. Stefani HA. Org. Lett. 2004; 6: 1135
  • 15 Huang X. Zhu L.-S. J. Chem. Soc., Perkin Trans. 1 1996; 767
  • 16 Dabdoub MJ. Begnini ML. Guerrero PG. Jr. Tetrahedron 1998; 54: 2371
  • 17 Pérez-Balado C. Markó IE. Tetrahedron 2006; 62: 2331
  • 18 Pérez-Balado C. Lucaccioni F. Markó IE. Tetrahedron Lett. 2005; 46: 4883
  • 19 Zhong P. Guo M.-P. J. Chem. Res., Synop. 2001; 370
  • 20 Sun A.-M. Huang X. Tetrahedron 1999; 55: 13201
  • 21 Dabdoub MJ. Begnini ML. Guerreiro PG. Jr. Baroni AC. M. J. Org. Chem. 2000; 65: 61
  • 22 Zhong P. Huang N.-P. Synth. Commun 2001; 31: 2423
  • 23 Al-Hassan MI. Synth. Commun. 2001; 31: 3027
  • 24 Dabdoub MJ. Cassol TM. Barbosa SL. Tetrahedron Lett. 1996; 37: 831
  • 25 Huang X. Ma Y. Synth. Commun. 1997; 27: 2407
  • 26 Yang Y. Huang X. Synth. Commun. 1997; 27: 345
  • 27 Huang X. Zhu L.-S. Synth. Commun. 1996; 26: 671
  • 28 Huang X. Wang J.-H. Synth. Commun. 2000; 30: 307
  • 29 Zhao H. Cai M. Synthesis 2002; 1347
  • 30 Silveira CC. Cella R. Vieira AS. J. Organomet. Chem. 2006; 691: 5861
  • 31 Huang X. Wu Z. Synthesis 2004; 2445
  • 32 Huang X. Xu L. Synthesis 2006; 231
  • 33 Kabalka GW. Venkataiah B. Tetrahedron Lett. 2002; 43: 3703
  • 34 Taniguchi N. J. Org. Chem. 2007; 72: 1241
  • 35 D’yakonov VA. Tuktarova RA. Tyumkina TV. Khalilov LM. Dzhemilev UM. Russ. Chem. Bull. 2010; 59: 1902
  • 36 D’yakonov VA. Galimova LF. Tyumkina TV. Dzhemilev UM. Russ. J. Org. Chem. 2012; 48: 1
  • 37 Ramazanov IR. Kadikova RN. Dzhemilev UM. Russ. Chem. Bull. 2011; 60: 99
  • 38 Ramazanov IR. Kadikova RN. Saitova ZR. Dzhemilev UM. Asian J. Org. Chem. 2015; 4: 1301
  • 39 Ramazanov IR. Kadikova RN. Saitova ZR. Nadrshina ZI. Dzhemilev UM. Synlett 2016; 27: 2567
  • 40 Kadikova RN. Ramazanov IR. Vyatkin AV. Dzhemilev UM. Synthesis 2017; 49: 1889
  • 41 Ramazanov IR. Kadikova RN. Dzhemilev UM. Zh. Org. Khim. 2013; 49: 335
  • 42 Kadikova RN. Ramazanov IR. Zosim TP. Dzhemilev UM. Synthesis 2015; 47: 2670
  • 43 Kadikova RN. Ramazanov IR. Zosim TP. Dzhemilev UM. J. Organomet. Chem. 2014; 763–764: 14
  • 44 Comprehensive Organic Chemistry: Sulphur, Selenium, Silicon, Boron, Organometallic Compounds. Vol. 3. Barton DH. R. Ollis WD. Pergamon Press; Oxford: 1979
  • 45 Muslukhav RR. Khalilov LM. Ramazanov IR. Sharipova AZ. Ibragimov AG. Dzhemilev UM. Russ. Chem. Bull. 1997; 46: 2082
  • 46 Negishi E. Kondakov DY. Choueiry D. Kasai K. Takahashi T. J. Am. Chem. Soc. 1996; 118: 9577
  • 47 Dzhemilev UM. Ibragimov AG. Zolotarev AP. Mendeleev Commun. 1992; 2: 135
  • 48 Al-Hassan MI. Synth. Commun. 2001; 31: 3027
  • 49 Van Horn DE. Negishi E.-i. J. Am. Chem. Soc. 1978; 100: 2252
  • 50 Negishi E. Van Horn DE. Yoshida T. J. Am. Chem. Soc. 1985; 107: 6639
  • 51 Rizvi MA. Guru S. Naqvi T. Kumar M. Kumbhar N. Akhoon S. Banday S. Singh SK. Bhushan S. Mustafa Peerzada G. Shah BA. Bioorg. Med. Chem. Lett. 2014; 24: 3440
  • 52 Okoronkwo AE. Rosário AR. Alves D. Savegnago L. Nogueira CW. Zeni G. Tetrahedron Lett. 2008; 49: 3252
  • 53 Frisch MJ. Trucks GW. Schlegel HB. Scuseria GE. Robb MA. Cheeseman JR. Scalmani G. Barone V. Mennucci B. Petersson GA. Nakatsuji H. Caricato M. Li X. Hratchian HP. Izmaylov AF. Bloino J. Zheng G. Sonnenberg JL. Hada M. Ehara M. Toyota K. Fukuda R. Hasegawa J. Ishida M. Nakajima T. Honda Y. Kitao O. Nakai H. Vreven T. Montgomery JA. Jr. Peralta JE. Ogliaro F. Bearpark M. Heyd JJ. Brothers E. Kudin KN. Staroverov VN. Kobayashi R. Normand J. Raghavachari K. Rendell A. Burant JC. Iyengar SS. Tomasi J. Cossi M. Rega N. Millam JM. Klene M. Knox JE. Cross JB. Bakken V. Adamo C. Jaramillo J. Gomperts R. Stratmann RE. Yazyev O. Austin AJ. Cammi R. Pomelli C. Ochterski JW. Martin RL. Morokuma K. Zakrzewski VG. Voth GA. Salvador P. Dannenberg JJ. Dapprich S. Daniels AD. Farkas Ö. Foresman JB. Ortiz JV. Cioslowski J. Fox DJ. Gaussian 09, Revision A.1 . Gaussian Inc; Wallingford: 2009
  • 54 Rampon PH. Giovenardi DS. Silva R. Rambo TL. Merlo RS. Schneider AA. Eur. J. Org. Chem. 2011; 35: 7066