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 2014; 46(23): 3191-3198
DOI: 10.1055/s-0034-1378652
DOI: 10.1055/s-0034-1378652
paper
Transition-Metal-Catalyzed Synthesis of 1,3-Diynes and Ynamides from 2-Bromo-1-iodoalkenes
Further Information
Publication History
Received: 26 March 2014
Accepted after revision: 24 July 2014
Publication Date:
03 September 2014 (online)
Abstract
Diynes and ynamides are important products in chemical synthesis. An efficient palladium-catalyzed homocoupling reaction of 2-bromo-1-iodoalkenes to give 1,3-diynes has been developed. The reactions are conducted under convenient conditions and provide products in moderate to excellent yields. Moreover, ynamides were synthesized from 2-bromo-1-iodoalkenes and carbamates, and it is noteworthy that this reaction is catalyzed by nanoparticulate copper(I) oxide to give ynamides in high yields.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
-
References
- 1a Tour JM. Chem. Rev. 1996; 96: 537
- 1b Nielsen MB, Diederich F. Chem. Rev. 2005; 105: 1837
- 1c Martin RE, Diederich F. Angew. Chem. Int. Ed. 1999; 38: 1350
- 1d Gholami M, Tykwinski RR. Chem. Rev. 2006; 106: 4997
- 1e Shi Shun AL. K, Tykwinski RR. Angew. Chem. Int. Ed. 2006; 45: 1034
- 2 Siemsen P, Livingston RC, Diederich F. Angew. Chem. Int. Ed. 2000; 39: 2632 ; and references cited therein
- 3a Navale BS, Bhat RG. RSC Adv. 2013; 3: 5220
- 3b He Y, Cai C. Catal. Sci. Technol. 2012; 2: 1126
- 3c Niu X, Li C, Li J, Jia X. Tetrahedron Lett. 2012; 53: 5559
- 3d Yin K, Li C, Li J, Jia X. Green Chem. 2011; 13: 591
- 3e Jia X, Yin K, Li C, Li J, Bian H. Green Chem. 2011; 13: 2175
- 3f Li Y.-N, Wang J.-L, He L.-N. Tetrahedron Lett. 2011; 52: 3485
- 3g Oishi T, Yamaguchi K, Mizuno N. ACS Catal. 2011; 1: 1351
- 3h Zhang S, Liu X, Wang T. Adv. Synth. Catal. 2011; 353: 1463
- 3i Wu T.-M, Huang S.-H, Tsai F.-Y. Appl. Organomet. Chem. 2011; 25: 395
- 3j Schmidt R, Thorwirth R, Szuppa T, Stolle A, Ondruschka B, Hopf H. Chem. Eur. J. 2011; 17: 8129
- 3k Alonso F, Melkonian T, Moglie Y, Yus M. Eur. J. Org. Chem. 2011; 2524
- 3l Kusuda A, Xu X.-H, Wang X, Tokunaga E, Shibata N. Green Chem. 2011; 13: 843
- 4a Wang D, Li J, Li N, Gao T, Hou S, Chen B. Green Chem. 2010; 12: 45
- 4b Li L, Wang J, Zhang G, Liu Q. Tetrahedron Lett. 2009; 50: 4033
- 4c Yin W, He C, Chen M, Zhang H, Lei A. Org. Lett. 2009; 11: 709
- 4d Adimurthy S, Malakar CC, Beifuss U. J. Org. Chem. 2009; 74: 5648
- 4e Kamata K, Yamaguchi S, Kotani M, Yamaguchi K, Mizuno N. Angew. Chem. Int. Ed. 2008; 47: 2407
- 4f Yamaguchi K, Kamata K, Yamaguchi S, Kotani M, Mizuno N. J. Catal. 2008; 258: 121
- 4g Li D, Yin K, Li J, Jia X. Tetrahedron Lett. 2008; 49: 5918
- 4h Liao Y, Fathi R, Yang Z. Org. Lett. 2003; 5: 909
- 4i Yadav JS, Reddy BV. S, Reddy KB, Gayathri KU, Prasad AR. Tetrahedron Lett. 2003; 44: 6493
- 4j Li J, Jiang H. Chem. Commun. 1999; 2369
- 5a Chen S.-N, Wu W.-Y, Tsai F.-Y. Green Chem. 2009; 11: 269
- 5b Yang F, Cui X, Li Y.-n, Zhang J, Ren G, Wu Y. Tetrahedron 2007; 63: 1963
- 5c Yan J, Wu J, Jin H.-x. J. Organomet. Chem. 2007; 692: 3636
- 5d Shi M, Qian H. Appl. Organomet. Chem. 2006; 20: 771
- 5e Batsanov AS, Collings JC, Fairlamb IJ. S, Holland JP, Howard JA. K, Lin Z, Marder TB, Parsons AC, Ward RC, Zhu J. J. Org. Chem. 2005; 70: 703
- 5f Li J.-H, Liang Y, Xie Y.-X. J. Org. Chem. 2005; 70: 4393
- 5g Li J.-H, Liang Y, Zhang X.-D. Tetrahedron 2005; 61: 1903
- 5h Fairlamb IJ. S, Bäuerlein PS, Marrison LR, Dickinson JM. Chem. Commun. 2003; 632
- 5i Lei A, Srivastava M, Zhang X. J. Org. Chem. 2002; 67: 1969
- 5j Liu Q, Burton DJ. Tetrahedron Lett. 1997; 38: 4371
- 6a Paixão MW, Weber M, Braga AL, de Azeredo JB, Deobald AM, Stefani HA. Tetrahedron Lett. 2008; 49: 2366
- 6b Nishihara Y, Okamoto M, Inoue Y, Miyazaki M, Miyasaka M, Takagi K. Tetrahedron Lett. 2005; 46: 8661
- 6c Nishihara Y, Ikegashira K, Hirabayashi K, Ando J, Mori A, Hiyama Y. J. Org. Chem. 2000; 65: 1780
- 7a Singh FV, Amaral MF. Z. J, Stefani HA. Tetrahedron Lett. 2009; 50: 2636
- 7b Oh CH, Reddy VR. Tetrahedron Lett. 2004; 45: 5221
- 7c Yoshida H, Yamaryo Y, Ohshita J, Kunai A. Chem. Commun. 2003; 1510
- 7d Shirakawa E, Nakao Y, Murota Y, Hiyama T. J. Organomet. Chem. 2003; 670: 132
- 8a Shen W, Thomas SA. Org. Lett. 2000; 2: 2857
- 8b Huang Z, Shang R, Zhang Z.-R, Tan X.-D, Xiao X, Fu Y. J. Org. Chem. 2013; 78: 4551
- 9a DeKorver KA, Li H, Lohse AG, Hayashi R, Lu Z, Zhang Y, Hsung RP. Chem. Rev. 2010; 110: 5064
- 9b Evano G, Coste A, Jouvin K. Angew. Chem. Int. Ed. 2010; 49: 2840
- 9c Wang X.-N, Yeom H.-S, Fang L.-C, He S, Ma Z.-X, Kedrowski BL, Hsung RP. Acc. Chem. Res. 2014; 47: 560
- 10 Hamada T, Ye X, Stahl SS. J. Am. Chem. Soc. 2008; 130: 833
- 11a Frederick MO, Mulder JA, Tracey MR, Hsung RP, Huang J, Kurtz KC. M, Shen L, Douglas CJ. J. Am. Chem. Soc. 2003; 125: 2368
- 11b Zhang X, Zhang Y, Huang J, Hsung RP, Kurtz KC. M, Oppenheimer J, Petersen ME, Sagamanova IK, Shen L, Tracey MR. J. Org. Chem. 2006; 71: 4170
- 11c Yao B, Liang Z, Niu T, Zhang Y. J. Org. Chem. 2009; 74: 4630
- 11d Dunetz JR, Danheiser RL. Org. Lett. 2003; 5: 4011
- 11e Zhang Y, Hsung RP, Tracey MR, Kurtz KC. M, Vera EL. Org. Lett. 2004; 6: 1151
- 12a Coste A, Karthikeyan G, Couty F, Evano G. Angew. Chem. Int. Ed. 2009; 48: 4381
- 12b Yang Y, Zhang X, Liang Y. Tetrahedron Lett. 2012; 53: 6557
- 13a Souto JA, Becker P, Iglesias Á, Muñiz K. J. Am. Chem. Soc. 2012; 134: 15505
- 13b Huang J, Xiong H, Hsung RP, Rameshkumar C, Mulder JA, Grebe TP. Org. Lett. 2002; 4: 2417
- 13c Jia W, Jiao N. Org. Lett. 2010; 12: 2000
- 13d Brücker D. Tetrahedron 2006; 62: 3809
- 14a Poulsen TB, Dickmeiss G, Overgaard J, Jørgensen KA. Angew. Chem. Int. Ed. 2008; 47: 4687
- 14b Simard-Mercier J, Jiang JL, Ho ML, Flynn AB, Ogilvie WW. J. Org. Chem. 2008; 73: 5899
- 14c Jiang B, Tian H, Huang Z-G, Xu M. Org. Lett. 2008; 10: 2737
- 14d Sun C, Camp JE, Weinreb SM. Org. Lett. 2006; 8: 1779
- 14e Lemay AB, Vulic KS, Ogilvie WW. J. Org. Chem. 2006; 71: 3615
- 14f Bellina F, Colzi F, Mannina L, Rossi R, Viel S. J. Org. Chem. 2003; 68: 10175
- 15a Chelucci G. Chem. Rev. 2012; 112: 1344
- 15b Liu J, Chen W, Wang L. RSC Adv. 2013; 3: 4723
- 15c Liu J, Chen W, Ji Y, Wang L. Adv. Synth. Catal. 2012; 354: 1585
- 15d Jouvin K, Bayle A, Legrand F, Evano G. Org. Lett. 2012; 14: 1652
- 15e Tan Z, Negishi E.-i. Angew. Chem. Int. Ed. 2006; 45: 762
- 15f Zeng X, Qian M, Hu Q, Negishi E.-i. Angew. Chem. Int. Ed. 2004; 43: 2259
- 15g Hwang GT, Son HS, Ku JK, Kim BH. J. Am. Chem. Soc. 2003; 125: 11241
- 15h Zeng X, Hu Q, Qian M, Negishi E.-i. J. Am. Chem. Soc. 2003; 125: 13636
- 16 Chen Z, Jiang H, Li Y, Qi C. Chem. Commun. 2010; 46: 8049
- 17a Xu H, Wang W, Zhu W. J. Phys. Chem. B 2006; 110: 13829
- 17b Zheng Z, Huang B, Wang Z, Guo M, Qin X, Zhang X, Wang P, Dai Y. J. Phys. Chem. C 2009; 113: 14448
- 17c Tan Y, Xue X, Peng Q, Zhao H, Wang T, Li Y. Nano Lett. 2007; 7: 3723
- 18 Amatore C, Blart E, Genêt JP, Jutand A, Lemaire-Audoire S, Savignac M. J. Org. Chem. 1995; 60: 6829 ; and references cited therein
- 19a Zhu Y, Shi Y. Org. Biomol. Chem. 2013; 11: 7451
- 19b Nador F, Fortunato L, Moglie Y, Vitale C, Radivoy G. Synthesis 2009; 4027
For selected reviews, see:
For reports on copper-catalyzed homocoupling reactions of terminal alkynes, see:
For Pd/Cu-catalyzed homocoupling reactions of terminal alkynes, see:
For Cu-catalyzed homocoupling reactions of internal alkynes, see:
For Pd-catalyzed homocoupling reactions of internal alkynes, see:
For selected reviews, see:
For selected applications of vic-dihaloalkenes, see:
For selected reviews and studies on gem-dihaloalkenes, see: