Communication
[1] G. Evano, A.-C. Gaumont, C. Alayrac, I. E. Wrona, J. R. Giguere, O. Delac-
roix, A. Bayle, K. Jouvin, C. Theunissen, J. Gatignol, A. C. Silvanus, Tetrahe-
dron 2014, 70, 1529.
[2] a) G. Evano, A. Coste, K. Jouvin, Angew. Chem. Int. Ed. 2010, 49, 2840;
Angew. Chem. 2010, 122, 2902; b) K. A. DeKorver, H. Li, A. G. Lohse, R.
Hayashi, Z. Lu, Y. Zhang, R. P. Hsung, Chem. Rev. 2010, 110, 5064; c) G.
Evano, K. Jouvin, A. Coste, Synthesis 2013, 45, 17; d) X.-N. Wang, H.-S.
Yeom, L.-C. Fang, S. He, Z.-X. Ma, B. L. Kedrowski, R. P. Hsung, Acc. Chem.
Res. 2014, 47, 560; e) G. Evano, C. Theunissen, M. Lecomte, Aldrichim.
Acta 2015, 48, 59.
[3] a) B. Witulski, C. Alayrac, Science of Synthesis: Houben-Weyl Methods of
Molecular Transformations (Ed.: A. de Meijere), Thieme, Stuttgart, Ger-
many, 2005, vol. 24, p. 933–956; b) V. A. Potapov, B. A. Trofimov, Science
of Synthesis: Houben-Weyl Methods of Molecular Transformations (Ed.: A.
de Meijere), Thieme, Stuttgart, Germany, 2005, vol. 24, p. 957–1005.
[4] a) K. M. Pietrusiewicz, M. Stankević, Science of Synthesis: Houben-Weyl
Methods of Molecular Transformations (Ed.: A. de Meijere), Thieme, Stutt-
gart, Germany, 2005, vol. 24, p. 1073–1086; b) A. Kondoh, H. Yorimitsu,
K. Oshima, Chem. Asian J. 2010, 5, 398; c) E. Bernoud, R. Veillard, C.
Alayrac, A.-C. Gaumont, Molecules 2012, 17, 14573.
[5] a) K. Jouvin, J. Heimburger, G. Evano, Chem. Sci. 2012, 3, 756; b) A. Lao-
uiti, K. Jouvin, M. M. Rammah, M. B. Rammah, G. Evano, Synthesis 2012,
44, 1491; c) K. Jouvin, R. Veillard, C. Theunissen, C. Alayrac, A.-C. Gau-
mont, G. Evano, Org. Lett. 2013, 15, 4592; d) C. Theunissen, M. Lecomte,
K. Jouvin, A. Laouiti, C. Guissart, J. Heimburger, E. Loire, G. Evano, Synthe-
sis 2014, 46, 1157; e) C. Tresse, C. Guissart, S. Schweizer, Y. Bouhoute, A.-
C. Chany, M.-L. Goddard, N. Blanchard, G. Evano, Adv. Synth. Catal. 2014,
356, 2051; f) G. Evano, K. Jouvin, C. Theunissen, C. Guissart, A. Laouiti, C.
Tresse, J. Heimburger, Y. Bouhoute, R. Veillard, M. Lecomte, A. Nitelet, S.
Schweizer, N. Blanchard, C. Alayrac, A.-C. Gaumont, Chem. Commun.
2014, 50, 10008; g) C. Theunissen, G. Evano, Org. Lett. 2014, 16, 4488.
[6] a) T. Kawasaki, Y. Miki, N. Inamoto, Chem. Lett. 1986, 1883; b) A. L. Braga,
F. Vargas, G. Zeni, C. C. Silveira, L. H. de Andrade, Tetrahedron Lett. 2002,
43, 4399; c) X. Huang, Z. Wu, Synthesis 2004, 2445; d) X. Huang, L. Xu,
Synthesis 2006, 231.
[10]
a) F. Slowinski, C. Aubert, M. Malacria, Tetrahedron Lett. 1999, 40, 5849;
b) O. Buisine, C. Aubert, M. Malacria, Synthesis 2000, 985; c) F. Slowinski,
C. Aubert, M. Malacria, J. Org. Chem. 2003, 68, 378; d) M. Schelper, O.
Buisine, S. Kozhushkov, C. Aubert, A. de Meijere, M. Malacria, Eur. J. Org.
Chem. 2005, 3000; e) G. Nishida, K. Noguchi, M. Hirano, K. Tanaka, Angew.
Chem. Int. Ed. 2007, 46, 3951; Angew. Chem. 2007, 119, 4025; f) B. Heller,
A. Gutnov, C. Fischer, H.-J. Drexler, A. Spannenberg, D. Redkin, C. Sunder-
mann, B. Sundermann, Chem. Eur. J. 2007, 13, 1117; g) S. Doherty, J. G.
Knight, C. H. Smyth, R. W. Harrington, W. Clegg, Org. Lett. 2007, 9, 4925;
h) A. Kondoh, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2007, 129, 6996;
i) S. Doherty, C. H. Smyth, R. W. Harrington, W. Clegg, Organometallics
2008, 27, 4837; j) G. Nishida, S. Ogaki, Y. Yokozawa, K. Noguchi, K. Tanaka,
Org. Lett. 2008, 10, 2849; k) G. Nishida, K. Noguchi, M. Hirano, K. Tanaka,
Angew. Chem. Int. Ed. 2008, 47, 3410; Angew. Chem. 2008, 120, 3458; l)
F. Mori, N. Fukawa, K. Noguchi, K. Tanaka, Org. Lett. 2011, 13, 362.
a) X. Yang, D. Matsuo, Y. Suzuma, J.-K. Fang, F. Xu, A. Orita, J. Otera, S.
Kajiyama, N. Koumura, K. Hara, Synlett 2011, 16, 2402; b) L. Peng, F. Xu,
Y. Suzuma, A. Orita, J. Otera, J. Org. Chem. 2013, 78, 12802.
W. Jiang, G. Allan, X. Chen, J. J. Fiordeliso, O. Linton, P. Tannenbaum, J.
Xu, P. Zhu, J. Gunnet, K. Demarest, S. Lundeen, Z. Sui, Steroids 2006, 71,
949.
[11]
[12]
[13]
M. Arisawa, M. Onoda, C. Hori, M. Yamaguchi, Tetrahedron Lett. 2006, 47,
5211. For an alternative and straightforward entry to alkynylphosphines,
see: I. P. Beletskaya, V. V. Afanasiev, M. A. Kazankova, I. V. Efimova, Org.
Lett. 2003, 5, 4309.
J. Hu, N. Zhao, B. Yang, G. Wang, L.-N. Guo, Y.-M. Liang, S.-D. Yang, Chem.
Eur. J. 2011, 17, 5516.
[14]
[15]
Y. Wang, J. Gan, L. Liu, H. Yuan, Y. Gao, Y. Liu, Y. Zhao, J. Org. Chem. 2014,
79, 3678.
[16] C. C. Chen, J. Waser, Chem. Commun. 2014, 50, 12923.
[17] a) J. Yang, T. Chen, Y. Zhou, S. Yin, L.-B. Han, Chem. Commun. 2015, 51,
3549; b) T. Wang, S. Chen, A. Shao, M. Gao, Y. Huang, A. Lei, Org. Lett.
2015, 17, 118. For the direct alkynylation of dialkylphosphites and
hydrogen isopropyl phenylphosphinate, also see ref.[20]
[18] A single example of the alkynylation of diphenylphosphine oxide with
phenylethynyl copper was reported in the course of our studies, see: L.
Liu, Y. Wu, Z. Wang, J. Zhu, Y. Zhao, J. Org. Chem. 2014, 79, 6816.
[19] R. D. Stephens, C. E. Castro, J. Org. Chem. 1963, 28, 3313.
[20] Y. Gao, G. Wang, L. Chen, P. Xu, Y. Zhao, Y. Zhou, L.-B. Han, J. Am. Chem.
Soc. 2009, 131, 7956.
[7] D. Lecerclé, M. Sawicki, F. Taran, Org. Lett. 2006, 8, 4283.
[8] a) B. O. Ashburn, R. G. Carter, L. N. Zakharov, J. Am. Chem. Soc. 2007,
129, 910; b) S. Doherty, C. H. Smyth, R. W. Harrington, W. Clegg, Organo-
metallics 2009, 28, 5273.
[9] a) S. G. A. van Assema, C. G. J. Tazelaar, G. Bas de Jong, J. H. van Maarse-
veen, M. Schakel, M. Lutz, A. L. Spek, J. C. Slootweg, K. Lammertsma,
Organometallics 2008, 27, 3210; b) E. A. Slutsky Smith, G. Molev, M. Boto-
shansky, M. Gandelman, Chem. Commun. 2011, 47, 319; c) X. He, P.
Zhang, J.-B. Lin, H. V. Huynh, S. E. Navarro Muñoz, C.-C. Ling, T. Baumgart-
ner, Org. Lett. 2013, 15, 5322.
Received: November 16, 2015
Published Online: January 15, 2016
Eur. J. Org. Chem. 2016, 633–638
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