Synlett 2014; 25(12): 1638-1642
DOI: 10.1055/s-0033-1341269
synpacts
© Georg Thieme Verlag Stuttgart · New York

Comparing Well-Defined Manganese, Iron, Cobalt, and Nickel Ketone Hydrosilylation Catalysts

Ryan J. Trovitch*
Department of Chemistry & Biochemistry, Arizona State University, Tempe, AZ 85287, USA   Fax: +1(480)9652747   Email: ryan.trovitch@asu.edu
› Author Affiliations
Further Information

Publication History

Received: 01 March 2014

Accepted after revision: 26 March 2014

Publication Date:
08 May 2014 (online)


Abstract

A brief review of manganese-catalyzed hydrosilylation is presented along with a personal account of how the design for the highly active catalyst, (Ph2PPrPDI)Mn, was conceived. The reductive transformations achieved using this catalyst are described and put into further context by comparing the observed activities with those attained for leading late first-row transition-metal catalysts.

 
  • References

  • 1 Enthaler S, Junge K, Beller M. Angew. Chem. Int. Ed. 2008; 47: 3317
    • 2a Gaillard S, Renaud J.-L. ChemSusChem 2008; 1: 505
    • 2b Troegel D, Stohrer J. Coord. Chem. Rev. 2011; 255: 1440
  • 3 Bullock RM. Catalysis without Precious Metals . Wiley-VCH; Weinheim: 2010
  • 4 Haynes WM. CRC Handbook of Chemistry and Physics: A Ready-Reference Book of Chemical and Physical Data. Taylor and Francis; Boca Raton: 2013. 94th ed

    • For examples, see:
    • 5a Zhang W, Loebach JL, Wilson SR, Jacobsen EN. J. Am. Chem. Soc. 1990; 112: 2801
    • 5b Fürstner A, Majima K, Martin R, Krause H, Kattnig E, Goddard R, Lehmann CW. J. Am. Chem. Soc. 2008; 130: 1992
    • 5c Czaplik WM, Mayer M, Cvengroš J, von Wangelin AJ. ChemSusChem 2009; 2: 396
    • 5d Fürstner A. Angew. Chem. Int. Ed. 2009; 48: 1364
    • 5e Morris RH. Chem. Soc. Rev. 2009; 38: 2282
    • 5f Chen MS, White MC. Science 2010; 327: 566
    • 6a Speier JL, Webster JA, Barnes GH. J. Am. Chem. Soc. 1957; 79: 974
    • 6b Hitchcock PB, Lappert MF, Warhurst NJ. W. Angew. Chem., Int. Ed. Engl. 1991; 30: 438
  • 7 Mukhopadhyay TK, Flores M, Groy TL, Trovitch RJ. J. Am. Chem. Soc. 2014; 136: 882
  • 8 Pratt SL, Faltynek RA. J. Organomet. Chem. 1983; 258: C5
  • 9 Hilal HS, Abu-Eid M, Al-Subu M, Khalaf S. J. Mol. Catal. 1987; 39: 1
  • 10 Mao Z, Gregg BT, Cutler AR. J. Am. Chem. Soc. 1995; 117: 10139 ; as part of this effort, (CO)5MnC(O)Me, (CO)5MnMe, and (CO)5MnBr were found to catalyze ester hydrosilylation, albeit less efficiently than (PPh3)(CO)4MnC(O)Me
  • 11 Cavanaugh M. D., Gregg B. T., Cutler A. R.; Organometallics; 1996, 15: 2764; as part of this study, (CO)5MnC(O)4-C6H4Me, (CO)5MnC(O)Me, (CO)5MnMe, and (CO)5MnBr were found to catalyze ketone hydrosilylation far less efficiently than (PPh3)(CO)4MnC(O)Me.
  • 12 Hanna PK, Gregg BT, Cutler AR. Organometallics 1991; 10: 31
  • 13 Cavanaugh MD, Gregg BT, Chiulli RJ, Cutler AR. J. Organomet. Chem. 1997; 547: 173
  • 14 Mao Z, Gregg BT, Cutler AR. Organometallics 1998; 17: 1993
  • 15 Son SU, Paik S.-J, Lee IS, Lee Y.-A, Chung YK, Seok WK, Lee HN. Organometallics 1999; 18: 4114
  • 16 Son SU, Paik S.-J, Chung YK. J. Mol. Catal. A: Chem. 2000; 151: 87
  • 17 Igarashi M, Fuchikami T. Tetrahedron Lett. 2001; 42: 1945
  • 18 The slow conversion of DMF into Me3N (≤1 h–1) has also been achieved using (η5-C5H5)Mn(CO)3 at 120 °C. See: Arias-Ugarte R, Sharma HK, Morris AL. C, Pannell KH. J. Am. Chem. Soc. 2012; 134: 848
  • 19 Zheng J, Chevance S, Darcel C, Sortais J.-B. Chem. Commun. 2013; 49: 10010
  • 20 Chidara VK, Du G. Organometallics 2013; 32: 5034
  • 21 Schroeder MA, Wrighton MS. J. Am. Chem. Soc. 1976; 98: 551
  • 22 Bart SC, Lobkovsky E, Chirik PJ. J. Am. Chem. Soc. 2004; 126: 13794
  • 23 Trovitch RJ, Lobkovsky E, Bill E, Chirik PJ. Organometallics 2008; 27: 1470
    • 24a de Bruin B, Bill E, Bothe E, Weyhermüller T, Wieghardt K. Inorg. Chem. 2000; 39: 2936
    • 24b Knijnenburg Q, Gambarotta S, Budzelaar PH. M. Dalton Trans. 2006; 5442
  • 25 Ben-Daat H, Hall GB, Groy TL, Trovitch RJ. Eur. J. Inorg. Chem. 2013; 4430
  • 26 Ruddy AJ, Kelly CM, Crawford SM, Wheaton CA, Sydora OL, Small BL, Stradiotto M, Turculet L. Organometallics 2013; 32: 5581
  • 27 Yang J, Tilley TD. Angew. Chem. Int. Ed. 2010; 49: 10186
  • 28 Tondreau AM, Lobkovsky E, Chirik PJ. Org. Lett. 2008; 10: 2789
  • 29 Tondreau AM, Darmon JM, Wile BM, Floyd SK, Lobkovsky E, Chirik PJ. Organometallics 2009; 28: 3928
  • 30 Brunner H, Amberger K. J. Organomet. Chem. 1991; 417: C63
  • 31 Niu Q, Sun H, Li X, Klein H.-F, Flörke U. Organometallics 2013; 32: 5235
  • 32 Chakraborty S, Krause JA, Guan H. Organometallics 2009; 28: 582
  • 33 Bheeter LP, Henrion M, Brelot L, Darcel C, Chetcuti MJ, Sortais J.-B, Ritleng V. Adv. Synth. Catal. 2012; 354: 2619
  • 34 We recently reported the preparation of α-diimine-ligated Ni complexes that mediate ketone and alkyne hydrosilylation based on the methodology described herein: Porter TM, Hall GB, Groy TL, Trovitch RJ. Dalton Trans. 2013; 42: 14689