RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
PDF herunterladen
Synlett 2008(10): 1427-1439
DOI: 10.1055/s-2008-1078414
DOI: 10.1055/s-2008-1078414
ACCOUNT
© Georg Thieme Verlag Stuttgart · New YorkMechanistic Studies on the Roles of Cosolvents and Additives in Samarium(II)-Based Reductions
Weitere Informationen
Received
19 January 2008
Publikationsdatum:
16. Mai 2008 (online)
Publikationsverlauf
Publikationsdatum:
16. Mai 2008 (online)
Abstract
This account describes work, performed by my research group during the past decade, designed to understand the mechanistic roles of cosolvents and additives in reductions involving samarium(II) iodide (SmI2). Emphasis is placed on studies designed to elucidate the roles of the cosolvent hexamethylphosphoramide (HMPA) and proton donors (water, alcohols, and glycols) in the mechanisms of important bond-forming reactions and reductions initiated by SmI2.
1 Background and Introduction
1.1 Project Inception
2 Mechanistic Studies on the Role of Hexamethylphosphoramide in the Reactions of Samarium(II) Iodide
3 Impact of Proton Donors on the Mechanism of Substrate Reduction
4 Conclusions and Future Work
Key words
samarium(II) iodide - electron transfer - hexamethylphosphoramide - proton donors - reductions
- 1
Girard P.Namy JL.Kagan HB. J. Am. Chem. Soc. 1980, 102: 2693MissingFormLabel - 2
Davis TA.Chopade PR.Hilmersson G.Flowers RA. Org. Lett. 2005, 7: 119 - 3
Chopade PR.Davis TA.Prasad E.Flowers RA. Org. Lett. 2004, 6: 2685 - 4
Concellon JM.Rodriguez-Solla H. Eur. J. Org. Chem. 2006, 613 - 5
Kamochi Y.Kudo T.Masuda T.Takadate A. Chem. Pharm. Bull. 2005, 53: 1017 - 6
Davies SG.Rodriguez-Solla H.Tamayo JA.Garner AC.Smith AD. Chem. Commun. (Cambridge) 2004, 2502 - 7
Mikami K.Yoshida A. Tetrahedron 2001, 57: 889 - 8
Kunishima M.Nakata D.Sakuma T.Kono K.Sato S.Tani S. Chem. Pharm. Bull. 2001, 49: 97 - 9
Kabata M.Suzuki T.Takabe K.Yoda H. Tetrahedron Lett. 2006, 47: 1607 - 10
Chiara JL.Garcia A.Cristobal-Lumbroso G. J. Org. Chem. 2005, 70: 4142 - 11
Holemann A.Reissig HU. Chem. Eur. J. 2004, 10: 5493 - 12
Concellon JM.Rodriguez-Solla H.Llavona R. J. Org. Chem. 2003, 68: 1132 - 13
Riber D.Skrydstrup T. Org. Lett. 2003, 5: 229 - 14
Masson G.Py S.Vallee Y. Angew. Chem. Int. Ed. 2002, 41: 1772 - 15
Desvergnes S.Py S.Vallee Y. J. Org. Chem. 2005, 70: 1459 - 16
Rivkin A.de Turiso FGL.Nagashima T.Curran DP. J. Org. Chem. 2004, 69: 3719 - 17
Howells DM.Barker SM.Watson FC.Light ME.Hursthouse MB.Kilburn JD. Org. Lett. 2004, 6: 1943 - 18
Zheng XL.Xu XL.Zhang YM. Synlett 2003, 2062 - 19
Saint-Dizier AC.Kilburn JD. Tetrahedron Lett. 2002, 43: 6201 - 20
Jaber N.Fiaud JC.Collin J. Tetrahedron Lett. 2001, 42: 9157 - 21
Giuseppone N.Collin J. Tetrahedron 2001, 57: 8989 - 22
Boffey RJ.Whittingham WG.Kilburn JD. J. Chem. Soc., Perkin Trans. 1 2001, 487 - 23
Watson FC.Kilburn JD. Tetrahedron Lett. 2000, 41: 10341 - 24
Huang L.-L.Xu M.-H.Lin G.-Q. J. Am. Chem. Soc. 2006, 128: 5624 - 25
Cho MS.Lee IS.Kang SH.Kim YH. Chem. Eur. J. 2005, 11: 1452 - 26
Molander GA.Etter JB.Zinke PW. J. Am. Chem. Soc. 1987, 109: 453 - 27
Evans WJ.Bloom I.Hunter WE.Atwood JL. J. Am. Chem. Soc. 1981, 103: 6507 - 28
Evans WJ.Hughes LA.Hanusa TP. J. Am. Chem. Soc. 1984, 106: 4270 - 29
Curran DP.Totleben MJ. J. Am. Chem. Soc. 1992, 114: 6050 - 30
Molander GA.McKie JA. J. Am. Chem. Soc. 1991, 56: 4112 - 31
Hasegawa E.Curran DP. J. Org. Chem. 1993, 58: 5008 - 32
Shabangi M.Flowers RA. Tetrahedron Lett. 1997, 38: 1137MissingFormLabel - 33
Hou Z.Wakatsuki Y. J. Chem. Soc., Chem. Commun. 1994, 1205 - 34
Evans WJ.Gummersheimer TS.Ziller JW. J. Am. Chem. Soc. 1995, 117: 8999MissingFormLabel - 35
Hou Z.Zhang Y.Wakatsuki Y. Bull. Chem. Soc. Jpn. 1997, 70: 149 - 36
Shotwell JB.Sealy JM.Flowers RA. J. Org. Chem. 1999, 64: 5251MissingFormLabel - 37a
Kuhlman ML.Flowers RA. Tetrahedron Lett. 2000, 41: 8049 - 37b
See also ref. 3.
- 38
Shotwell JB.Flowers RA. Tetrahedron Lett. 1998, 39: 8063 - 40
Enemærke RJ.Hertz T.Skrydstrup T.Daasbjerg K. Chem. Eur. J. 2000, 6: 3747 - 41
Prasad E.Flowers RA. J. Am. Chem. Soc. 2002, 124: 6895 - 42
Hubig SM.Rathorey R.Kochi JK. J. Am. Chem. Soc. 1999, 121: 617 - 43
Smitha MA.Prasad E.Gopidas KR. J. Am. Chem. Soc. 2001, 123: 1159 - 44
Cabri W.Candiani I.Colombo M.Franzoi L.Bedeschi A. Tetrahedron Lett. 1995, 36: 949 - 45
Shabangi M.Sealy JM.Fuchs JR.Flowers RA. Tetrahedron Lett. 1998, 39: 4429 - 46
Fukuzawa S.Mutoh K.Tsuchimoto T.Hiyama T. J. Org. Chem. 1996, 61: 5400 - 47
Evans WJ.Drummond DK.Zhang H.Atwood JL. Inorg. Chem. 1988, 27: 575 - 48
Brady ED.Clark DL.Keogh DW.Scott BL.Watkin JG. J. Am. Chem. Soc. 2000, 122: 7007 - 49
Prasad E.Knettle BW.Flowers RA. J. Am. Chem. Soc. 2002, 124: 14663 - 50
Kim M.Knettle BW.Dahlén A.Hilmersson G.Flowers RA. Tetrahedron 2003, 59: 10397 - 51
Prasad E.Knettle BW.Flowers RA. J. Am. Chem. Soc. 2004, 126: 6891 - 52a
Dahlén A.Hilmersson G. Chem. Eur. J. 2003, 9: 1123 - 52b
Dahlén A.Hilmersson G.Knettle BW.Flowers RA. J. Org. Chem. 2003, 68: 4870 - 52c
Dahlén A.Sundgren A.Lahmann M.Oscarson S.Hilmersson G. Org. Lett. 2003, 5: 4085 - 52d
Dahlén A.Petersson A.Hilmersson G. Org. Biomol. Chem. 2003, 1: 2423 - 52e
See also ref. 2
- 52f
Ankner T.Hilmersson G. Tetrahedron Lett. 2007, 48: 5707 - 53
Dahlén A.Hilmersson G. J. Am. Chem. Soc. 2005, 127: 8340 - 54a
Yoshida A.Mikami K. Synlett 1997, 1375MissingFormLabel - 54b
Yoshida A.Manamoto T.Inanaga J.Mikami K. Tetrahedron Lett. 1998, 39: 1777MissingFormLabel - 55a
Keck GE.Wager CA.Sell T.Wager TT. J. Org. Chem. 1999, 64: 2172 - 55b
Edmonds DJ.Muir KW.Procter DJ. J. Org. Chem. 2003, 68: 3190 - 56
Hoz S.Yacovan A.Bilkis I. J. Am. Chem. Soc. 1996, 118: 261 - 57
Tarnopolsky A.Hoz S. Org. Biomol. Chem. 2007, 5: 3801 - 58
Chopade PR.Prasad E.Flowers RA. J. Am. Chem. Soc. 2004, 126: 44MissingFormLabel - 59a
Kamochi Y.Kusudo T.Daiichi CPS.Fukuoka J. Chem. Lett. 1993, 1495 - 59b
Kamochi Y.Kusudo T.Daiichi CPS.Fukuoka J. Heterocycles 1993, 36: 2383 - 60
Jensen CM.Lindsay KB.Taaning RH.Karaffa J.Hansen AM.Skrydstrup T. J. Am. Chem. Soc. 2005, 127: 6544 - 61
Andrieux CP.Gallardo I.Saveant J.-M.Su K.-B. J. Am. Chem. Soc. 1986, 108: 638 - 62
Prasad E.Flowers RA. J. Am. Chem. Soc. 2005, 127: 18093 - 63
Matsukawa S.Hinakubo Y. Org. Lett. 2003, 5: 1221 - 64
Miller RS.Sealy JM.Fuchs JR.Shabangi M.Flowers RA. J. Am. Chem. Soc. 2000, 122: 7718MissingFormLabel - 65
White JP.Deng H.Boyd EP.Gallucci J.Shore SG. Inorg. Chem. 1994, 33: 1685 - 66
Vestergren M.Gustafsson B.Johansson A.Håkansson M. J. Organomet. Chem. 2004, 689: 1723 - 67
Teprovich JA.Balili MN.Pintauer T.Flowers RA. Angew. Chem. Int. Ed. 2007, 46: 8160 - 68a
Pederson HL.Christensen TB.Enemærke RJ.Daasbjerg K.Skrydstrup T. Eur. J. Org. Chem. 1999, 565 - 68b
Christensen TB.Riber D.Daasbjerg K.Skrydstrup T. Chem. Commun. (Cambridge) 1999, 2051 - 68c
Dahlén A.Hilmersson G. Tetrahedron Lett. 2001, 42: 5565 - 68d
Aspinall HC.Greeves N.Valla C. Org. Lett. 2005, 7: 1919
References
Shotwell, J. B. unpublished results.