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Synthesis 2018; 50(16): 3205-3216
DOI: 10.1055/s-0037-1609575
DOI: 10.1055/s-0037-1609575
special topic
Palladium-Catalyzed Decarboxylative Benzylation of Acetylides and Enolates
We thank the National Science Foundation (CHE-1465172) and the Kansas Bioscience Authority Rising Star program for financial support. Support for the NMR instrumentation was provided by NSF Academic Research Infrastructure Grant No. 9512331, NIH Shared Instrumentation Grant No. S10RR024664, and NSF Major Research Instrumentation Grant No. 0320648.Further Information
Publication History
Received: 15 May 2018
Accepted after revision: 14 June 2018
Publication Date:
30 July 2018 (online)
Published as part of the Special Topic Modern Coupling Approaches and their Strategic Applications in Synthesis
Abstract
Benzylic alkylation of enolates and acetylides has been achieved through the use of a decarboxylative benzylation strategy. Previous research in this area is often limited by the need for extended conjugation in the electrophiles that are coupled. Herein, we report that the use of 1,1'-bis(diphenylphosphino)ferrocene (dppf) ligand allows the coupling of simple benzyl electrophiles with enolates, while the use of XPhos ligand promotes the decarboxylative couplings of propiolates.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609575.
- Supporting Information
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References
- 1a Bras JL. Muzart J. Eur. J. Org. Chem. 2016; 2565
- 1b Hayashi Y. Nishizawa M. Sakan T. Tetrahedron Lett. 1977; 33: 2509
- 1c Legros J.-Y. Toffano M. Fiaud J.-C. Tetrahedron 1995; 51: 3235
- 1d Legros J.-Y. Primault G. Toffano M. Rivière M.-A. Fiaud J.-C. Org. Lett. 2000; 2: 433
- 1e Legros J.-Y. Boutros A. Fiaud J.-C. Toffano M. J. Mol. Catal. A: Chem. 2003; 196: 21
- 1f Kuwano R. Kondo Y. Matsuyama Y. J. Am. Chem. Soc. 2003; 125: 12104
- 1g Kuwano R. Kondo Y. Org. Lett. 2004; 6: 3545
- 1h Mukai T. Hirano K. Satoh T. Miura M. Org. Lett. 2010; 12: 1360
- 1i Trost BM. Czabaniuk LC. J. Am. Chem. Soc. 2010; 132: 15534
- 1j Trost BM. Czabaniuk LC. J. Am. Chem. Soc. 2012; 134: 5778
- 1k Zhu Y. Rawal VH. J. Am. Chem. Soc. 2012; 134: 111
- 1l Tabuchi S. Hirano K. Miura M. Angew. Chem. Int. Ed. 2016; 55: 6973
- 2a Zhou Q. Cobb KM. Tan T. Watson MP. J. Am. Chem. Soc. 2016; 138: 12057
- 2b Zhou Q. Srinivas HD. Dasgupta S. Watson MP. J. Am. Chem. Soc. 2013; 135: 3307
- 2c Zhang S. Taylor BL. H. Ji C. Gao Y. Harris MR. Hanna LE R. Jarvo ER. Houk KN. Hong X. J. Am. Chem. Soc. 2017; 139: 12994
- 2d Lucas EL. Jarvo E. Nat. Rev. Chem. 2017; 1: 65
- 2e Dawson DD. Jarvo ER. Org. Process Res. Dev. 2015; 19: 1356
- 2f Tollefson EJ. Hanna LE. Jarvo ER. Acc. Chem. Res. 2015; 48: 2344
- 3a Pérez I. Sestelo JP. Sarandeses LA. J. Am. Chem. Soc. 2001; 123: 4155
- 3b Qian M. Negishi E. Tetrahedron Lett. 2005; 46: 2927
- 4a Torregrosa RR. Ariyarathna Y. Chattopadhyay K. Tunge JA. J. Am. Chem. Soc. 2010; 132: 9280
- 4b Weaver JD. Recio A. Grenning AJ. Tunge JA. Chem. Rev. 2011; 111: 1846
- 4c Fields WH. Chruma JJ. Org. Lett. 2010; 12: 316
- 4d Grünberg MF. Gooßen LJ. Chem. Eur. J. 2013; 19: 7334
- 4e Mendis SN. Tunge JA. Chem. Commun. 2016; 7695
- 4f Mendis SN. Tunge JA. Org. Lett. 2015; 17: 5164
- 4g Yang M.-H. Hunt JR. Sharifi N. Altman RA. Angew. Chem. Int. Ed. 2016; 55: 9080
- 4h Recio AIII. Heinzman JD. Tunge JA. Chem. Commun. 2012; 142
- 4i Shang R. Huang Z. Xiao X. Lu X. Fu Y. Liu L. Adv. Synth. Catal. 2012; 354: 2465
- 4j Montgomery TD. Zhu Y. Kagawa N. Rawal VH. Org. Lett. 2013; 15: 1140
- 4k Kuwano R. Kusano H. Org. Lett. 2008; 10: 1979
- 5 Maji T. Ramakumar K. Tunge JA. Chem. Commun. 2014; 14045
- 6a Larsen CH. Anderson KW. Tundel RE. Buchwald SL. Synlett 2006; 2941
- 6b Pottier LR. Peyrat J.-F. Alami M. Brion J.-D. Synlett 2004; 1503
- 6c Zhang W.-W. Zhang X.-G. Li J.-H. J. Org. Chem. 2010; 75: 5259
- 7 Tardibono LP. Jr. Patzner J. Cesario C. Miller MJ. Org. Lett. 2009; 11: 4076
- 8 Komiya S. Synthesis of Organometallic Compounds. A Practical Guide. John Wiley & Sons; New York: 1997: 290
- 9 Cabello JA. Campelo JM. Luna GD. Marinas JM. J. Org. Chem. 1986; 51: 1786
- 10 Oh K.-B. Kim S.-H. Lee J. Cho W.-J. Lee T. Kim S. J. Med. Chem. 2004; 47: 2418
- 11 Reisman SE. Cherney AH. Tetrahedron 2014; 3259
- 12 Gansäuer A. Stock C. Fielenbach D. Geich-Gimbel D. Adv. Synth. Catal. 2003; 345: 1017
- 13 Cruz AC. F. Miller ND. Willis MC. Org. Lett. 2007; 9: 4391
- 14 Rosa D. Orellana A. Org. Lett. 2011; 13: 110
- 15 Ma S. He Q. Zhang X. J. Org. Chem. 2005; 70: 3336
- 16 Li C. Li W. Wang J. Tetrahedron Lett. 2009; 50: 2533
- 17 Li C. Wang J. J. Org. Chem. 2007; 72: 7431
- 18 Biradar DP. Gau H.-M. Chem. Commun. 2011; 10467