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-00000084.xml
Synthesis 2014; 46(19): 2617-2621
DOI: 10.1055/s-0034-1378358
DOI: 10.1055/s-0034-1378358
paper
A Highly Active CuI/TMEDA Catalytic System for the Coupling Reaction of Acid Chlorides with Terminal Alkynes under Solvent-Free Conditions
Weitere Informationen
Publikationsverlauf
Received: 31. März 2014
Accepted after revision: 29. Mai 2014
Publikationsdatum:
08. Juli 2014 (online)
Abstract
A highly efficient copper(I) iodide/N,N,N′,N′-tetramethylethylenediamine (CuI/TMEDA) catalytic system for the synthesis of ynones has been developed. A variety of terminal alkynes, including 4-iodophenylacetylene, were smoothly coupled with acid chlorides in the presence 2 mol% CuI and 5 mol% TMEDA to afford the corresponding ynones in good to excellent yields in a short time. It is noteworthy that the reaction is conducted under solvent-free conditions at room temperature.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
-
References
- 1 These authors contributed equally to this study.
- 2a Karpov AS, Müller TJ. J. Org. Lett. 2003; 5: 3451
- 2b Van den Hoven BG, El Ali B, Alper H. J. Org. Chem. 2000; 65: 4131
- 2c Wang XJ, Tan J, Zhang L. Org. Lett. 2000; 2: 3107
- 2d Kel’in AV, Sromek AW, Gevorgyan V. J. Am. Chem. Soc. 2001; 123: 2074
- 2e Bagley MC, Hughes DD, Lloyd R, Powers VE. C. Tetrahedron Lett. 2001; 42: 6585
- 2f Bagley MC, Hughes DD, Taylor PH. Synlett 2003; 259
- 2g Karpov AS, Merkul E, Oeser T, Müller TJ. J. Chem. Commun. 2005; 2581
- 2h Waldo JP, Larock RC. Org. Lett. 2005; 7: 5203
- 2i Karpov AS, Merkul E, Oeser T, Müller TJ. J. Eur. J. Org. Chem. 2006; 13: 2991
-
3a Wender PA, Bi FC, Brodney MA, Gosselin F. Org. Lett. 2001; 3: 2105
- 3b Sneddon HF, Gaunt MJ, Ley SV. Org. Lett. 2003; 5: 1147
-
4a Utimoto K, Miwa H. Tetrahedron Lett. 1981; 22: 4277
- 4b Wills MS. B, Danheiser RL. J. Am. Chem. Soc. 1998; 120: 9378
- 4c Jeevanam A, Narkunan K, Ling YC. J. Org. Chem. 2001; 66: 6014
- 4d Kel’in AV, Gevorgyan V. J. Org. Chem. 2002; 67: 95
- 4e Grotjahn DB, Van S, Combs D, Lev DA, Schneider C, Rideout M, Meyer C, Hernande G, Mejorado L. J. Org. Chem. 2002; 67: 9200
- 5a Tohda Y, Sonogashira K, Hagihara N. Synthesis 1977; 777
- 5b Walton DR. M, Waugh F. J. Organomet. Chem. 1972; 37: 45
- 5c Newman H. J. Org. Chem. 1973; 38: 2254
- 5d Yadav JS, Reddy BV. S, Reddy MS. Synlett 2003; 1722
- 5e Wang J.-X, Wei B, Hu Y, Liu Z, Fu Y. Synth. Commun. 2001; 31: 3527
- 5f Cox RJ, Ritson DJ, Dane TA, Berge J, Charmant JP. H, Kantacha A. Chem. Commun. 2005; 1037
- 5g Chen L, Li C.-J. Org. Lett. 2004; 6: 3151
- 5h Guo M, Li D, Zhang Z. J. Org. Chem. 2003; 68: 10172
-
6 Davis RB, Scheiber DH. J. Am. Chem. Soc. 1956; 78: 1675
- 7a Normant JF. Synthesis 1972; 63
- 7b Logue MW, Moore GL. J. Org. Chem. 1975; 40: 131
- 7c Bourgain M, Normant JF. Bull. Soc. Chim. Fr. 1973; 2137
- 8 Fontaine M, Chauvelier J, Barchewitz P. Bull. Soc. Chim. Fr. 1962; 2145
- 9 Compagnon PL, Grosjean B, Lacour M. Bull. Soc. Chim. Fr. 1975; 779
- 10 Yashina OG, Zarva TV, Vereshchagin LI. Zh. Org. Khim. 1967; 3: 219 ; Chem. Abstr. 1967, 66, 94664g
- 11 Vereshchagin LI, Yashina OG, Zarva TV. Zh. Org. Khim. 1966; 2: 1895 ; Chem. Abstr. 1967, 66, 46070
- 12 Alonso DA, Najera C, Pacheco MC. J. Org. Chem. 2004; 69: 1615
- 13a Oh CH, Reddy VR. Tetrahedron Lett. 2004; 45: 5221
- 13b Oh CH, Reddy VR. Tetrahedron Lett. 2004; 45: 8545
- 13c Nishihara Y, Saito D, Inoue E, Okada Y, Miyazaki M, Inoue Y, Takagi K. Tetrahedron Lett. 2010; 51: 306
- 14 Logue MW, Teng K. J. Org. Chem. 1982; 47: 2549
- 15a Mohamed Ahmed MS, Mori A. Org. Lett. 2003; 5: 3057
- 15b Hao W, Sha J, Sheng S, Cai M. J. Mol. Catal. A: Chem. 2009; 298: 94
- 15c Genelot M, Bendjeriou A, Dufaud V, Djakovitch L. Appl. Catal. A: Gen. 2009; 369: 125
- 15d Genelot M, Dufaud V, Djakovitch L. Adv. Synth. Catal. 2013; 355: 2604
- 16 Zanina AS, Shergina SI, Sokolov IE, Kotlyarevskii IL. Izv. Akad. Nauk SSSR, Ser. Khim. 1981; 1158 ; Chem. Abstr. 1981, 49, 7276
- 17 Chowdhury C, Kundu NG. Tetrahedron Lett. 1996; 37: 7323
- 18 Hajime I, Kikuo A, I-Iiro-omi S, Aldra H. Tetrahedron Lett. 1997; 38: 3977
- 19 Yin W, He C, Chen M, Zhang H, Lei A. Org. Lett. 2009; 11: 709
- 20a Shi Y, Zhao B, Zhu Y. Org. Lett. 2013; 15: 992
- 20b Wang B, Bonin M, Micouin L. J. Org. Chem. 2005; 70: 6126
- 20c Sun W, Wang Y, Wu X, Yao X. Green Chem. 2013; 15: 2356
- 20d Iman M, Bouyssou P, Chenault J. Synthesis 1990; 631
- 20e Yuan H, Zhang W, Shen Y, Shan L, Sun Q, Yu S. Synth. Commun. 2013; 43: 2817
- 20f Delieto C, Eagon S, Haddenham D, Kim J, McDonald W, Saavedra J, Singaram B. J. Org. Chem. 2010; 75: 7717
- 20g Tanaka K, Otake Y, Wada A, Noguchi K, Hirano M. Org. Lett. 2007; 9: 2203
- 20h Chen Z, Fei X.-D, Ge Z.-Y, Tang T, Zhu Y.-M, Ji S.-J. J. Org. Chem. 2013; 78: 3170
- 20i Larock RC, Mehta S, Waldo JP. J. Org. Chem. 2008; 73: 6666
- 20j Cheng C.-H, Gandeepan P, Parthasarathy K, Su T.-H. Adv. Synth. Catal. 2012; 354: 457
- 20k Gupta S, Kundu B, Mandadapu AK, Sharma S, Gauniyal HM. Tetrahedron Lett. 2011; 52: 4288
- 20l Tambade PJ, Patil YP, Nandurkar NS, Bhanage BM. Synlett 2008; 886
- 20m Keivanloo A, Bakherad M, Bahramian B, Rahmani M, Naghi Taheri SA. Synthesis 2011; 325