Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2017; 49(16): 3643-3653
DOI: 10.1055/s-0036-1588177
DOI: 10.1055/s-0036-1588177
paper
Highly Efficient Synthesis of Multi-Substituted Allenes from Propargyl Acetates and Organoaluminum Reagents Mediated by Palladium
Supported by: Sichuan Provincial Department of Science and Technology support program (2015NZ0033)Supported by: Southwest University for Nationalities graduate student innovation funds (CX2016SZ052)
Further Information
Publication History
Received: 18 February 2017
Accepted after revision: 28 March 2017
Publication Date:
04 May 2017 (online)
Abstract
A simple and mild catalytic SN2′ substitution reaction of propargyl acetates with organoaluminum reagents is reported. The SN2′ substitution reaction of propargyl acetates with organoaluminum reagents mediated by Pd(PhP3)2Cl2 (1 mol%)/PPh3 (2 mol%)/K2CO3 in tetrahydrofuran at 60 °C for 3–4 hours afforded the corresponding multi-substituted allenes in good yields (up to 94%) with high selectivities (up to 99%). The process was simple and easily performed, which offers an efficient method to synthesize the multi-substituted allene derivatives.
Key words
allenes - palladium - propargyl acetates - organoaluminum reagent - SN2′ substitution reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588177.
- Supporting Information
-
References
- 1a Modern Allene Chemistry. Vol. 1 and 2. Krause N. Hashmi AS. K. Wiley-VCH; Weinheim: 2004
- 1b Ma SM. Palladium-Catalyzed Two- or Three-Component Cyclization of Functionalized Allenes. In Palladium in Organic Synthesis. Tsuji J. Springer; Berlin: 2005: 183-210
- 1c Brasholz M. Reissig H.-U. Zimmer R. Acc. Chem. Res. 2009; 42: 45
- 1d Ye JT. Ma SM. Acc. Chem. Res. 2014; 47: 989
- 1e Bruneau C. Renaud J.-L. Allenes and Cumulenes. In Comprehensive Organic Functional Group Transformations II. Vol. 1. Katritzky AR. Taylor RJ. K.. Cossy J. Elsevier; Oxford: 2005: 1019−1081
- 2a Zimmer R. Dinesh CU. Nandanan E. Khan FA. Chem. Rev. 2000; 100: 3067
- 2b Lu X. Zhang C. Xu Z. Acc. Chem. Res. 2001; 34: 535
- 2c Bates RW. Satcharoen V. Chem. Soc. Rev. 2002; 31: 12
- 2d Ma SM. Acc. Chem. Res. 2003; 36: 701
- 2e Brandsma L. Nedolya NA. Synthesis 2004; 735
- 2f Ma SM. Chem. Rev. 2005; 105: 2829
- 2g Ma SM. Aldrichimica Acta 2007; 40: 91
- 2h Ma SM. Acc. Chem. Res. 2009; 42: 1679
- 2i Yu SC. Ma SM. Angew. Chem. Int. Ed. 2012; 51: 3074 ; Angew. Chem. 2012, 128, 3128
- 2j Alcaide B. Almendros P. Cembellín S. Martinez del Campo T. Fernández I. Chem. Commun. 2013; 49: 1282
- 2k Alcaide B. Almendros P. Alonso JM. Fernández I. J. Org. Chem. 2013; 78: 6688
- 2l Lechel T. Pfrengle F. Reissig HU. Zimmer R. ChemCatChem 2013; 5: 2100
- 2m Alcaide B. Almendros P. Aragoncillo C. Chem. Soc. Res. 2014; 43: 3106
- 2n Lledó A. Pla-Quintana A. Roglans A. Chem. Soc. Res. 2016; 45: 2010
- 3a Hoffmann-Röder A. Krause N. Angew. Chem. Int. Ed. 2004; 43: 1196 ; Angew. Chem. 2004, 116, 1216
- 3b Kim H. Williams LJ. Curr. Opin. Drug Discovery Dev. 2008; 11: 870
- 3c Ugurchieva TM. Veselovsky VV. Russ. Chem. Rev. 2009; 78: 337
- 3d Saito N. Tanaka Y. Sato Y. Org. Lett. 2009; 11: 4124
- 4a Leclère M. Fallis AG. Angew. Chem. Int. Ed. 2008; 47: 568 ; Angew. Chem. 2008, 120, 578
- 4b Rivera-Fuentes P. Diederich F. Angew. Chem. Int. Ed. 2012; 51: 2818 ; Angew. Chem. 2012, 124, 2872
- 5a Sydnes LK. Chem. Rev. 2003; 103: 1133
- 5b Krause N. Hoffmann-Röder A. Tetrahedron 2004; 60: 11671
- 5c Brummond KM. Deforrest JE. Synthesis 2007; 795
- 5d Krause N. Belting V. Deutsch C. Erdsack J. Fan H. Gockel B. Hoffmann-Röder A. Morita N. Volz F. Pure Appl. Chem. 2008; 80: 1063
- 5e Ogasawara M. Tetrahedron: Asymmetry 2009; 20: 259
- 5f Yu SC. Ma SM. Chem. Commun. 2011; 47: 5384
- 5g Neff RK. Frantz DE. ACS Catal. 2014; 4: 519
- 6a Kolakowski RV. Bolte B. Odabachian Y. Gagosz F. J. Am. Chem. Soc. 2010; 132: 7294
- 6b Kalek M. Stawinski J. Adv. Synth. Catal. 2011; 353: 1741
- 6c Xiao Q. Xia Y. Li H. Zhang Y. Wang J. Angew. Chem. Int. Ed. 2011; 50: 1114 ; Angew. Chem. 2011, 123, 1146
- 6d Yu XZ. Zhang JL. Adv. Synth. Catal. 2011; 353: 1265
- 6e Hossain ML. Ye F. Zhang Y. Wang JB. J. Org. Chem. 2013; 78: 1236
- 6f Hashimoto T. Sakata K. Tamakuni F. Dutton MJ. Maruoka K. Nat. Chem. 2013; 5: 240
- 6g Wu Z. Berhal F. Zhao MM. Zhang ZG. Ayad T. Ratovelomanana-Vidal V. ACS Catal. 2014; 4: 44
- 6h Li QH. Jeng JY. Gau HM. Eur. J. Org. Chem. 2014; 7916
- 6i Li QH. Liao JW. Huang YL. Chiang RT. Gau HM. Org. Biomol. Chem. 2014; 12: 7634
- 6j Gangadhararao G. Kumara Swamy KC. Tetrahedron 2014; 70: 2643
- 6k Wei W. Wen JW. Yang DS. Guo MY. Wang YY. You JM. Wang H. Chem. Commun. 2015; 51: 768
- 6l Tang XJ. Han YL. Ma SM. Org. Lett. 2015; 18: 1176
- 6m Ruchti J. Carreria EM. Org. Lett. 2016; 18: 2174
- 6n Periasamy M. Reddy PO. Satyanarayana I. Mohan L. Athukuri Edukondalu A. J. Org. Chem. 2016; 81: 987
- 7a Ma SM. Yu SC. Yin SH. J. Org. Chem. 2003; 68: 8996
- 7b Yokota M. Fuchibe K. Ueda M. Mayumi Y. Ichikawa J. Org. Lett. 2009; 11: 3994
- 8a Brossat M. Heck MP. Mioskowski C. J. Org. Chem. 2007; 72: 5938
- 8b Phadke N. Findlater M. Organometallics 2014; 33: 16
- 9a Kuang JK. Ma SM. J. Am. Chem. Soc. 2010; 132: 1786
- 9b Jiang GJ. Zheng QH. Dou M. Zhuo LG. Meng W. Yu ZX. J. Org. Chem. 2013; 78: 11783
- 9c Gurubrahamam R. Periasamy M. J. Org. Chem. 2013; 78: 1463
- 10 Wang YL. Zhang WL. Ma SM. J. Am. Chem. Soc. 2013; 135: 11517
- 11a Deutsch C. Lipshutz BH. Krause N. Angew. Chem. Int. Ed. 2007; 46: 1650 ; Angew. Chem. 2007, 119, 1677
- 11b Ito H. Sasaki Y. Sawamura M. J. Am. Chem. Soc. 2008; 130: 15774
- 11c Li HL. Müller D. Guénée L. Alexakis A. Org. Lett. 2013; 15: 334
- 12a Li Q.-H. Ding Y. Yang X.-J. Chin. Chem. Lett. 2014; 25: 1296
- 12b Li Q.-H. Ding Y. Huang NW. Chin. Chem. Lett. 2014; 25: 1469
- 13 Mahrwald R. Quint S. Tetrahedron 2000; 56: 7463
- 14 Kessler SN. Bäckvall JE. Angew. Chem. Int. Ed. 2016; 55: 3734 ; Angew. Chem. 2016, 128, 3798
For some recent reviews on the chemistry of allenes, see:
For a review on the natural products and pharmaceuticals containing allene unit(s), see:
For recent reviews on the synthesis of allenes, see:
For selected recent reports on the synthesis of allenes, see: