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Synlett 2011(16): 2275-2278
DOI: 10.1055/s-0030-1261226
DOI: 10.1055/s-0030-1261226
SYNPACTS
© Georg Thieme Verlag
Stuttgart ˙ New YorkN-Heterocyclic Carbene (NHC)-Catalyzed All-Carbon [4+2] Cycloaddition-Decarboxylation
Further Information
Received
24 July 2011
Publication Date:
08 September 2011 (online)
Publication History
Publication Date:
08 September 2011 (online)
Abstract
NHCs activate a diverse range of materials and thereby play a central role in modern reaction discovery. Our studies have focused on the application of NHCs as Lewis base catalysts. We recently developed an all-carbon [4+2] cycloaddition-decarboxylation that typifies this type of catalysis. Herein, the discovery of this methodology, its context and scope are discussed.
Key words
catalysis - acyl azolium - N-heterocyclic carbenes - cycloaddition - cyclohexadiene
- 1
Ugai T.Tanaka S.Dokawa S. J. Pharm. Soc. Jpn. 1943, 63: 296 - 2
Breslow R. J. Am. Chem. Soc. 1958, 80: 3719MissingFormLabel - For reviews on NHC catalysis, see:
- 3a
Enders D.Niemeier O.Henseler A. Chem. Rev. 2007, 107: 5606MissingFormLabel - 3b
Marion N.Díez-González S.Nolan SP. Angew. Chem. Int. Ed. 2007, 46: 2988MissingFormLabel - 3c
Nair V.Vellalath S.Babu BP. Chem. Soc. Rev. 2008, 37: 2691MissingFormLabel - 3d
Moore JL.Rovis T. Top. Curr. Chem. 2009, 290: 77MissingFormLabel - 3e
Phillips EM.Chan A.Scheidt KA. Aldrichimica Acta 2009, 42: 55MissingFormLabel - 3f
Vora HH.Rovis T. Aldrichimica Acta 2011, 44: 3MissingFormLabel - 4
Castells J.Llitjos H.Moreno-Mañas M. Tetrahedron Lett. 1977, 18: 205 - For examples with cyanide, see:
- 5a
Corey EJ.Gilman NW.Ganem RE. J. Am. Chem. Soc. 1968, 90: 5616MissingFormLabel - 5b
Corey EJ.Katzenellenbogen JA.Gilman NW.Roman SA.Erickson BW. J. Am. Chem. Soc. 1968, 90: 5618MissingFormLabel - For other examples of oxidations of acyl anions to acyl azoliums, see:
- 6a
Ohta S.Hayakawa S.Nishimura K.Okamoto M. Chem. Pharm. Bull. 1987, 135: 1058MissingFormLabel - 6b
Miyashita A.Suzuki Y.Nagasaki I.Iwamoto K.-I.Higashino T. Chem. Pharm. Bull. 1997, 45: 1254MissingFormLabel - For examples of acyl azolium catalysis, see:
- 7a
Chow KY.-K.Bode JW. J. Am. Chem. Soc. 2004, 126: 8126MissingFormLabel - 7b
Reynolds NT.ReaddeAlaniz J.Rovis T. J. Am. Chem. Soc. 2004, 126: 9518MissingFormLabel - For selected studies involving acyl azoliums, see:
- 7c
Burstein C.Glorius F. Angew. Chem. Int. Ed. 2004, 43: 6205MissingFormLabel - 7d
Sohn SS.Rosen EL.Bode JW. J. Am. Chem. Soc. 2004, 126: 14370MissingFormLabel - 7e
Chan A.Scheidt KA. Org. Lett. 2005, 7: 905MissingFormLabel - 7f
Zeitler K. Org. Lett. 2006, 8: 637MissingFormLabel - 7g
Maki BE.Chan A.Phillips EM.Scheidt KA. Org. Lett. 2007, 9: 371MissingFormLabel - 7h
Vora HU.Rovis T. J. Am. Chem. Soc. 2007, 129: 13796MissingFormLabel - 7i
Guin J.De Sarkar S.Grimme S.Studer A. Angew. Chem. Int. Ed. 2008, 47: 8727MissingFormLabel - 7j
Maki BE.Patterson EV.Cramer CJ.Scheidt KA. Org. Lett. 2009, 11: 3942MissingFormLabel - 7k
Philips EM.Wadamoto M.Roth HS.Ott AW.Scheidt KA. Org. Lett. 2009, 11: 105MissingFormLabel - 7l
Vora HU.Rovis T. J. Am. Chem. Soc. 2010, 132: 2860MissingFormLabel - 7m
De Sarkar S.Grimme S.Studer A. J. Am. Chem. Soc. 2010, 132: 1190MissingFormLabel - 7n
Thai K.Wang L.Dudding T.Bilodeau F.Gravel M. Org. Lett. 2010, 12: 5708MissingFormLabel - 7o
De Sarkar S.Studer A. Org. Lett. 2010, 12: 1992MissingFormLabel - 7p
De Sarkar S.Biswas A.Song CH.Studer A. Synthesis 2011, 1974MissingFormLabel - 8For a review on Lewis base catalysis, see:
- 8
Denmark SE.Beutner GL. Angew. Chem. Int. Ed. 2008, 47: 1560 - For reviews on NHC nucleophilicity, see:
- 9a
Mayr H.Breugst M.Maji B. Angew. Chem. Int. Ed. 2011, 50: 6915MissingFormLabel - 9b
Dröge T.Glorius F. Angew. Chem. Int. Ed. 2010, 49: 6940MissingFormLabel - 10For the Mukaiyama aldol reaction, see:
- 10
Song JJ.Tan Z.Reeves JT.Yee NK.Senanayake CH. Org. Lett. 2007, 9: 1013; for other examples of C-Si activation, see articles cited therein - 11
Lee K.-S.Zhugralin AR.Hoveyda AH. J. Am. Chem. Soc. 2009, 131: 7253MissingFormLabel - 12a
Fischer C.Smith SW.Powell DA.Fu GC. J. Am. Chem. Soc. 2006, 128: 1472 For recent extentions of this type of reactivity, see:Matsuoka SI.Ota Y.Washio A.Katada A.Ichioka K.Takagi K.Suzuki M. Org. Lett. 2011, 13: 3722MissingFormLabel - 12b
Biju AT.Padmanaban M.Wurz NE.Glorius F. Angew. Chem. Int. Ed. 2011, 50: DOI: 10.1002/anie.201103555MissingFormLabel - 13a
Grasa GA.Kissling RM.Nolan SP. Org. Lett. 2002, 4: 3583MissingFormLabel - 13b
Nyce GW.Lamboy JA.Connor EF.Waymouth RM.Hedrick JL. Org. Lett. 2002, 4: 3587MissingFormLabel - NHC-catalyzed transesterification with amino alcohols and mechanistic comments:
- 13c
Movassaghi M.Schmidt MA. Org. Lett. 2005, 7: 2453MissingFormLabel - 13d
Schmidt MA.Müller P.Movassaghi M. Tetrahedron Lett. 2008, 49: 4316MissingFormLabel - 14
Song JJ.Tan Z.Reeves JT.Fandrick DR.Yee NK.Senanayake CH. Org. Lett. 2008, 10: 877 - 15a
Ryan SJ.Candish L.Lupton DW. J. Am. Chem. Soc. 2009, 131: 14176MissingFormLabel - 15b
Candish L.Lupton DW. Org. Lett. 2010, 12: 4836MissingFormLabel - For a related reaction with mechanistic discussion, see:
- 16a
Kaeobamrung J.Mahatthananchai J.Zheng P.Bode JW. J. Am. Chem. Soc. 2010, 132: 8810MissingFormLabel - 16b
Mahatthananchai J.Zheng P.Bode JW. Angew. Chem. Int. Ed. 2011, 50: 1673MissingFormLabel - For related reactions, see:
- 17a
De Sarkar S.Studer A. Angew. Chem. Int. Ed. 2010, 49: 9266MissingFormLabel - 17b
Zhu Z.-Q.Xiao J.-C. Adv. Synth. Catal. 2010, 352: 2455MissingFormLabel - 17c
Zhu Z.-Q.Zheng X.-L.Jiang N.-F.Wan X.Xiao J.-C. Chem. Commun. 2011, 47: 8670MissingFormLabel - 17d
Rong Z.-Q.Jia M.-Q.You S.-L. Org. Lett. 2011, 13: 4080MissingFormLabel - 18
Bappert E.Müller P.Fu G. Chem. Commun. 2006, 2604 - 19
Poisson T.Dalla V.Papamicaël C.Dupas G.Marsais F.Levacher V. Synlett 2007, 381 - 20
Woods PA.Morrill LC.Lebl T.Slawin AMZ.Bragg RA.Smith AD. Org. Lett. 2010, 12: 2660 - For NHC-catalyzed reactions involving β-lactones, see:
- 21a
Nair V.Vellalath S.Poonoth M.Suresh E. J. Am. Chem. Soc. 2006, 128: 8736MissingFormLabel - 21b
Chiang P.-C.Kaeobamrung J.Bode JW. J. Am. Chem. Soc. 2007, 129: 3520MissingFormLabel - 21c
Wadamoto M.Phillips EM.Reynolds TE.Scheidt KA. J. Am. Chem. Soc. 2007, 129: 10098MissingFormLabel - 21d
He M.Bode JW. J. Am. Chem. Soc. 2008, 130: 418MissingFormLabel - 21e
Kaeobamrung J.Bode JW. Org. Lett. 2009, 11: 677MissingFormLabel - 21f
Phillips EM.Roberts JM.Scheidt KA. Org. Lett. 2010, 12: 2830MissingFormLabel - For a useful review on 2-pyrones and 2-pyridones in synthesis, see:
- 22a
Afarinkia K.Vinader V.Nelson TD.Posner GH. Tetrahedron 1992, 48: 9111MissingFormLabel - For recent examples in catalysis, see:
- 22b
Soh JY.-T.Tan CH.
J. Am. Chem. Soc. 2009, 131: 6904MissingFormLabel - For selected studies in total synthesis, see:
- 22c
Martin SF.Rüeger H.Williamson SA.Grzejszczak S. J. Am. Chem. Soc. 1987, 109: 6124MissingFormLabel - 22d
Nelson HM.Stoltz BM. Org. Lett. 2008, 10: 25MissingFormLabel - 22e
Baran PS.Burns NZ. J. Am. Chem. Soc. 2006, 128: 3908MissingFormLabel - For methodologies, see:
- 22f
Li L.Chase CE.West FG. Chem. Commun. 2008, 4025MissingFormLabel - 22g
Afarinkia K.Abdullahi MH.Scowen IJ. Org. Lett. 2010, 12: 5564MissingFormLabel - 23
Ryan SJ.Candish L.Lupton DW. J. Am. Chem. Soc. 2011, 133: 4694MissingFormLabel - 25For a review on vinylogous reactivity, see:
- 25
Denmark SE.Heemstra JR.Beutner GL. Angew. Chem. Int. Ed. 2005, 44: 4682
References
Ryan, S. J.; Paddon-Row, M. Lupton, D. W. unpublished results.