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Synthesis 2011(16): 2600-2608
DOI: 10.1055/s-0030-1260130
DOI: 10.1055/s-0030-1260130
SPECIALTOPIC
© Georg Thieme Verlag
Stuttgart ˙ New York
A Facile Synthesis of α-Fluoro Ketones Catalyzed by [Cp*IrCl2]2
Further Information
Received
3 June 2011
Publication Date:
21 July 2011 (online)
Publication History
Publication Date:
21 July 2011 (online)
Abstract
Allylic alcohols are isomerized into enolates (enols) by [Cp*IrCl2]2. The enolates react with Selectfluor present in the reaction media. This method produces α-fluoro ketones as single constitutional isomers in high yields.
Key words
iridium - fluorine - isomerization - alcohols - fluoro ketones
- Supporting Information for this article is available online:
- Supporting Information
- 1
Stork G.Rosen P.Goldman N.Coombs RV.Tsuji J. J. Am. Chem. Soc. 1965, 87: 275 - For early examples, see:
-
2a
Gazzard LJ.Motherwell WB.Sandham DA. J. Chem. Soc., Perkin Trans. 1 1999, 979 -
2b
Matsuda I.Takahashi K.Sato S. Tetrahedron Lett. 1990, 31: 5331 ; and references cited therein - For examples of Rh-catalyzed reductive aldol reaction using hydrogen as reducing agent, see:
-
3a
Jang H.-Y.Krische MJ. Acc. Chem. Res. 2004, 37: 653 -
3b
Ngai M.-Y.Kong J.-R.Krische MJ. J. Org. Chem. 2007, 72: 1063 - For recent examples of Rh-catalyzed reductive aldol reaction using silanes as reducing agents, see:
-
4a
Nishiyama H.Shiomi T.Tsuchiya Y.Matsuda I.
J. Am. Chem. Soc. 2005, 127: 6972 -
4b
Fuller NO.Morken JP. Synlett 2005, 1459 -
4c
Ito JI.Shiomi T.Nishiyama H. Adv. Synth. Catal. 2006, 348: 1235 -
4d
Shiomi T.Ito J.-I.Yamamoto Y.Nishiyama H. Eur. J. Org. Chem. 2006, 5594 -
4e
Shiomi T.Nishiyama H. Org. Lett. 2007, 9: 1651 -
4f
Hashimoto T.Ito J.-i.Nishiyama H. Tetrahedron 2008, 64: 9408 - For recent catalytic reductive aldol couplings using other metals, see:
-
5a
Lam HW.Joensuu PMA. Org. Lett. 2005, 7: 4225 -
5b
Lam HW.Murray GJ.Firth JD. Org. Lett. 2005, 7: 5743 -
5c
Deschamp J.Chuzel O.Hannedouche J.Riant O. Angew. Chem. Int. Ed. 2006, 45: 1292 -
5d
Chuzel O.Deschamp J.Chauster C.Riant O. Org. Lett. 2006, 8: 5943 -
5e
Zhao D.Oisaki K.Kanai M.Shibasaki M. Tetrahedron Lett. 2006, 47: 1403 -
5f
Zhao D.Oisaki K.Kanai M.Shibasaki M. J. Am. Chem. Soc. 2006, 128: 14440 -
5g
Welle A.Diez-Gonzalez S.Tinant B.Nolan SP.Riant O. Org. Lett. 2006, 8: 6059 -
5h
Lipshutz BH.Amorelli B.Unger JB. J. Am. Chem. Soc. 2008, 130: 14378 -
5i
Chrovian CC.Montgomery J. Org. Lett. 2007, 9: 537 -
5j
Shibata I.Kato H.Ishida T.Yasuda M.Baba A. Angew. Chem. Int. Ed. 2004, 43: 711 -
5k
Miura K.Yamada Y.Tomita M.Hosomi A. Synlett 2004, 1985 - 6
Cadierno V.García-Garrido SE.Gimeno J.Varela-Álvarez A.Sordo JA. J. Am. Chem. Soc. 2006, 128: 1360 -
7a
Wang M.Li C.-J. Tetrahedron Lett. 2002, 43: 3589 -
7b
Wang M.Yang X.-F.Li C.-J. Eur. J. Org. Chem. 2003, 998 -
7c
Yang X.-F.Wang M.Varma RS.Li C.-J. Org. Lett. 2003, 6: 657 -
7d
Yang X.-F.Wang M.Varma RS.Li C.-J. J. Mol. Catal. A: Chem. 2004, 214: 147 -
8a
Uma R.Davies M.Crévisy C.Grée R. Tetrahedron Lett. 2001, 42: 3069 -
8b
Crévisy C.Wietrich M.Le Boulaire V.Uma R.Grée R. Tetrahedron Lett. 2001, 42: 395 -
8c
Uma R.Gouault N.Crévisy C.Grée R. Tetrahedron Lett. 2003, 44: 6187 -
8d
Branchadell V.Crévisy C.Grée R. Chem. Eur. J. 2004, 10: 5795 -
8e
Cuperly D.Crévisy C.Grée R. Synlett 2004, 93 -
8f
Cuperly D.Petrignet J.Crévisy C.Grée R. Chem. Eur. J. 2006, 12: 3261 - 9
Mizuno A.Kusama H.Iwasawa N. Chem. Eur. J. 2010, 16: 8248 -
10a
Bartoszewicz A.Livendahl M.Martín-Matute B. Chem. Eur. J. 2008, 14: 10547 -
10b
Ahlsten N.Martín-Matute B. Adv. Synth. Catal. 2009, 351: 2657 -
11a
Müller K.Faeh C.Diederich F. Science 2007, 317: 1881 -
11b
Böhm H.-J.Banner D.Bendels S.Kansy M.Kuhn B.Müller K.Obst-Sander U.Stahl M. ChemBioChem 2004, 5: 637 -
11c
Jeschke P. ChemBioChem 2004, 5: 570 -
11d
Mikami K.Itoh Y.Yamanaka M. Chem. Rev. 2003, 104: 1 - 12
Lyons TW.Sanford MS. Chem. Rev. 2010, 110: 1147 -
13a
Nyffeler PT.Durón SG.Burkart MD.Vincent SP.Wong C.-H. Angew. Chem. Int. Ed. 2005, 44: 192 -
13b
Cahard D.Xu X.Couve-Bonnaire S.Pannecoucke X. Chem. Soc. Rev. 2010, 39: 558 -
13c
Lectard S.Hamashima Y.Sodeoka M. Adv. Synth. Catal. 2010, 352: 2708 -
13d
Kang YK.Kim DY. Curr. Org. Chem. 2010, 14: 917 -
13e
Brunet VA.O’Hagan D. Angew. Chem. Int. Ed. 2008, 47: 1179 -
13f
Pihko PM. Angew. Chem. Int. Ed. 2006, 45: 544 -
13g
Ibrahim H.Togni A. Chem. Commun. 2004, 1147 -
13h
Kwiatkowski P.Beeson TD.Conrad JC.MacMillan DWC. J. Am. Chem. Soc. 2011, 133: 1738 -
14a
Bélanger .Cantin K.Messe O.Tremblay M.Paquin J.-F. J. Am. Chem. Soc. 2007, 129: 1034 -
14b
Wang W.Jasinski J.Hammond GB.Xu B. Angew. Chem. Int. Ed. 2010, 49: 7247 -
14c
de Haro T.Nevado C. Adv. Synth. Catal. 2010, 352: 2767 - Nontransition-metal-catalyzed methods:
-
15a
Stavber G.Stavber S. Adv. Synth. Catal. 2010, 352: 2838 -
15b
Taylor SD.Kotoris CC.Hum G. Tetrahedron 1999, 55: 12431 -
15c
Davis FA.Kasu PVN. Org. Prep. Proced. Int. 1999, 31: 125 -
15d
Wilkinson JA. Chem. Rev. 1992, 92: 505 -
15e
Verniest G.Van Hende E.Surmont R.De Kimpe N. Org. Lett. 2006, 8: 4767 - 16
Zhang W.Hu J. Adv. Synth. Catal. 2010, 352: 2799 - 17
Ahlsten N.Martín-Matute B. Chem. Commun. 2011, 47: 8331 - 18
Hartwing JF.Bergman RG.Andersen RA. Organometallics 1991, 10: 3326 - 19
Kim JW.Koike T.Kotani M.Yamaguchi K.Mizuno N. Chem. Eur. J. 2008, 14: 4104 - 20
Onaran MB.Seto CT. J. Org. Chem. 2003, 68: 8136 - 21
Ling T.Chowdhury C.Kramer BA.Vong BG.Palladino MA.Theodorakis EA. J. Org. Chem. 2001, 66: 8843 - 22
Tamaru Y.Hojo M.Kawamura SI.Sawada S.Yoshida ZI. J. Org. Chem. 1987, 52: 4062 - 23
Aramini A.Brinchi L.Germani R.Savelli G. Eur. J. Org. Chem. 2000, 1793 - 24
Iwasaki M.Kobayashi Y.Li J.-P.Matsuzaka H.Ishii Y.Hidai M. J. Org. Chem. 1991, 56: 1922 - 25
Bunce RA.Nago T. J. Heterocycl. Chem. 2009, 46: 623 - 26
Bouziane A.Hélou M.Carboni B.Carreaux F.Demerseman B.Bruneau C.Renaud J.-L. Chem. Eur. J. 2008, 14: 5630 - 27
Kundu NG.Dasgupta SK.Chaudhuri LN.Mahanty JS.Spears CP.Shahinian AH. Eur. J. Med. Chem. 1993, 28: 473 - 28
Schmidt B. J. Org. Chem. 2004, 69: 7672 - 29
Bartoszewicz A.Martín-Matute B. Org. Lett. 2009, 11: 1749 - 30
Barluenga J.Fañanás FJ.Sanz R.Marcos C.Trabada M. Org. Lett. 2002, 4: 1587 - 31
Ishiyama T.Ahiko T.Miyaura N. J. Am. Chem. Soc. 2002, 124: 12414 - 32
Marion N.Gealageas R.Nolan SP. Org. Lett. 2007, 9: 2653 - 33
Deming TJ.Novak BM.Ziller JW. J. Am. Chem. Soc. 1994, 116: 2366 - 34
Herrmann AT.Saito T.Stivala CE.Tom J.Zakarian A. J. Am. Chem. Soc. 2010, 132: 5962