10.1002/adsc.201801334
Advanced Synthesis & Catalysis
congenial atmosphere and continuous support. The authors
sincerely thank Dr. A. P. John Pal for the helpful discussions.
2005, 53, 140; f) P. Michel, A. Rassat, Tetrahedron
Lett. 1999, 40, 8575; g) P. Bach, K. Nilsson, T.
Svensson, U. Bauer, L. G. Hammerland, A. Peterson,
A. Wallberg, K. Oesterlund, D. Karis, M. Boije, D.
Wensbo, Bioorg. Med. Chem. Lett. 2006, 16, 4788; h)
B. C. G. Soederberg, S. P. Gorugantula, C. R.
Howerton, J. L. Petersen, S. W. Dantale, Tetrahedron.
2009, 65, 7357.
References
[1] For a review on the chemistry and preparations of
terminal alkynes please see: a) D. Habrant, V. Rauhala,
A. M. P. Koskinen, Chem. Soc. Rev. 2010, 39, 2007;
For a review on the chemistry of terminal alkynes b) J.
P. Brand, Y. Li, J. Waser, Isr. J. Chem. 2013, 53, 901;
c) R. A. D. Arancon, C. S. K. Lin, C. Vargasc, R.
Luque, Org. Biomol. Chem. 2014, 12, 10; d) J.
Blanco-Urgoiti, L. Anorbe, G. Perez-Serrano,
Domínguez, J. Perez-Castells, Chem. Soc. Rev. 2004,
33, 32; e) F. Amblard, J. H. Cho, R. F. Schinazi, Chem.
Rev. 2009, 109, 4207; f) H. C. Kolb, M. G. Finn, K. B.
Sharpless, Angew. Chem., Int. Ed. 2001, 40, 2004.
[5] a) F. Diederich, P. J. Stang, R. R. Tykwinski,
Acetylene Chemistry: Chemistry, Biology and
Material Science; Wiley-VCH: Weinheim, Germany,
2005; b) N. El-Jaber, A. Estevez-Braun, A.G. Ravelo,
O. Munoz-Munoz, A. Rodriguez-Afaonso, J. R.
Murguia, J. Nat. Prod. 2003, 66, 722.
[6] A. K. Morri, Y. Thummala, V. R. Doddi, Org. Lett.
2015, 17, 4640.
[7] S. K. Moodapelly, G. V. M. Sharma, and V. R. Doddi,
[2] For a review on the preparations of internal alkynes
please see: K. Sonogashira, Y. Tohda, N. Hagihara,
Tetrahedron Lett. 1975, 16, 4467. a) R. Chinchilla, C.
Najera, Chem. Soc. Rev. 2011, 40, 5084; b) H. Doucet,
J. C. Hierso, Angew. Chem., Int. Ed. 2007, 46, 834; c)
U. H. F. Bunz, Chem. Rev. 2000, 100, 1605; d) M.
Zhang, T. Jia, C. Y. Wang, P. J. Walsh, J. Am. Chem.
Soc. 2015, 137, 10346; e) Y. Ji, N. Zhong, Z. Kang,
G. Yan, M. Zhao, Synlett. 2018, 29, 209. f) M. L. N.
Rao, D. N. Jadhav, P. Dasgupta, Org. Lett. 2010, 12,
2048; g) M. L. N. Rao, P. Dasgupta, V. N. Murty, RSC
Adv. 2015, 5, 24834; h) S. Kumar, S. Peruncheralathan,
H. Ila, H. Junjappa, Org. Lett. 2008. 10, 5; For a
review on the chemistry of internal alkynes please see.
i) K. Gilmore, I. V. Alabugin, Chem. Rev. 2011, 111,
6513; j) U. Wille, Chem. Rev. 2013, 113, 813; k) R.
Salvio, M. Moliterno, M. Bella, Asian J. Org. Chem.
2014, 3, 340; l) G. Zeni, R. C. Larock, Chem. Rev.
2004, 104, 2285; m) M. C. Willis, Chem. Rev. 2010,
110, 725; n) B. Godoi, R. F. Schumacher, G. Zeni,
Chem. Rev. 2011, 111, 2937.
Adv. Synth. Catal. 2017, 359, 1535.
[8] For the synthesis of 1,1-dibromoalkenes please see: a)
N. B. Desai, F. Ramirez, N. McKelvie, J. Am. Chem.
Soc. 1962, 84, 1745; b) D. Grandjean, P. Pale, J.
Chuche, Tetrahedron Lett. 1994, 35, 3529; c) H.
Rezaei, J. F. Normant, Synthesis. 2000, 2000, 109; For
a recent review, see: d) G. Chelucci, Chem. Rev. 2012,
112, 1344; For the chemistry on 1,1-dibromoalkenes
please se.. e) K. Jouvin, A. Coste, A. Bayle, F.
Legrand, G. Karthikeyan, K. Tadiparthi, G. Evano,
Organometallics. 2012, 31, 7933; f) Z. Whensheng, L.
Wei, K. Chunxiang, Progress in Chemistry. 2013, 25,
1149.
[9] a) P. Michel, A. Rassat, Tetrahedron Lett. 1999, 40,
8575; b) M. Matsumoto, K. Kuroda, Tetrahedron Lett.
1980, 21, 4021; c) O. Illa, X. Bagan, A. M Cazorla, C.
Lyon, A. Baceiredo, V. Branchadell, R. M. Ortuno. J.
Org. Chem. 2006, 71, 5320; d) E. W. Colvin, B. J.
Hamill, J. Chem. Soc., Chem. Commun. 1973, 151; e)
E. W. Colvin, B. J. Hamill, J. Chem. Soc., Perkin
Trans. 1977, 869; f) J. C. Gilbert, U. Weerasooriya, J.
Org. Chem. 1979, 44, 4997; g) K. Miwa, T. Aoyama,
T. Shioiri, Synlett. 1994, 107; h) K. Miwa, T. Aoyama,
T. Shioiri, Synlett. 1994, 109.
[3] For a review on the chemistry and preparations and
chemistry of enynes please see: a) C. Jahier, O. V.
Zatolochnaya, N. V. Zvyagintsev, V. P. Ananikov, V.
Gevorgyan, Org. Lett. 2012, 14, 2846; b) C. C.
Silveira, A. L. Braga, A. S. Vieira, G. Zeni, J. Org.
Chem. 2003, 68, 662; c) A. Tikad, A. Hamze, O.
Provot, J. D. Brion, M. Alami, Eur. J. Org. Chem.
2010, 725; d) M. Alami, F. Ferri, G. Linstrumelle,
Tetrahedron Lett. 1993, 34, 6403; e) Y. Wakatsuki, J.
Organomet. Chem. 2004, 689, 4092; f) M. Mori, Adv.
Synth. Catal. 2007, 349, 121; g) V. V. Pagar, T. V.
RajanBabu, Science. 2018, 361, 68; h) K. M. Miller, E.
A. Colby, K. S. Woodin, T. F. Jamison, Adv. Synth.
Catal. 2005, 347, 1533.
[10]a) S. Ohira, Synth. Commun. 1989, 19, 561; b) S.
Mꢀller, B. Liepold, G. J. Roth, H. J. Bestmann,
Synlett 1996, 1996, 521.
[11] For a latest effort to make in situ Ohira-Bestman
Org. Chem. 2014, 79, 9423.
[12] a) E. J. Corey, P. L. Fuchs, Tetrahedron Lett. 1972,
13, 3769; For recent developments on Corey-Fuchs
reaction b) S. Liu, X. Chen, Y. Hu, L. Yuan, S. Chen,
P. Wu, W. Wang, S. Zhang, W. Zhang, Adv. Synth.
Catal. 2015, 357, 553; c) R. M. Singh, D. Nandini, K.
C. Bharadwaj, T. Guptaa, R. P. Singh, Org. Biomol.
Chem., 2017, 15, 9979.
[4] For a recent review on 1-haloalkynes please see: a) W.
Wu, H. Jiang, Acc. Chem. Res. 2014, 47, 2483; b) J. P.
Brand, J. Waser, Chem. Soc. Rev. 2012, 41, 4165; For
recent reports on the peparations of 1-bromoalkynes
please see: c) M. Li, Y. Li, B. Zhao, F. Liang, L. Y.
Jin, RSC Adv. 2014, 4, 30046; d) D. Naskar, S. Roy, J.
Org. Chem. 1999, 64, 6896; e) M. Hashimoto, T.
Komano, K. Nabeta, Y. Hatanaka, Chem. Pharm. Bull.
[13] a) Y. Q. Fang, O. Lifchits, M. Lautens, Synlett. 2008,
413; b) C. Bryan, V. Aurregi, M. Lautens, Org. Synth.
2009, 86, 36.
5
This article is protected by copyright. All rights reserved.