Organometallics
Communication
(34) Elamari, H.; Meganem, F.; Herscovici, J.; Girard, C. Tetrahedron
Lett. 2011, 52 (6), 658.
(35) Yao, Z.; Yang, Y.; Chen, X.; Hu, X.; Zhang, L.; Liu, L.; Zhao, Y.;
Wu, H.-C. Anal. Chem. 2013, 85 (12), 5650.
(36) Jackson, W. R.; Perlmutter, P.; Smallridge, A. J. Aust. J. Chem.
1988, 41 (8), 1201.
(37) La Regina, G.; Silvestri, R.; Artico, M.; Lavecchia, A.; Novellino,
E.; Befani, O.; Turini, P.; Agostinelli, E. J. Med. Chem. 2007, 50 (5),
922.
(38) Klein, J.; Brenner, S. Tetrahedron 1970, 26 (10), 2345.
(39) West, R.; Chwang, T. L. J. Chem. Soc. D 1971, 813.
(40) Eberly, K. C.; Adams, H. E. J. Organomet. Chem. 1965, 3 (2),
165.
ACKNOWLEDGMENTS
■
We thank the Australian Research Council (DP170104722) for
funding and Prof. Steven Bull (Bath) for helpful discussions.
REFERENCES
■
(1) Harrison-Marchand, A.; Maddaluno, J. In Lithium Compounds in
Organic Synthesis; Wiley-VCH: Weinheim. Germany, 2014; pp 297−
328.
(2) Davies, S. G.; Fletcher, A. M.; Roberts, P. M.; Thomson, J. E.
Tetrahedron: Asymmetry 2012, 23 (15−16), 1111.
(3) Davies, S. G.; Smith, A. D.; Price, P. D. Tetrahedron: Asymmetry
2005, 16 (17), 2833.
(4) Andrews, P. C.; Koutsaplis, M.; Robertson, E. G. Organometallics
2009, 28 (6), 1697.
(5) Andrews, P. C.; Blair, V. L.; Border, E. C.; Peatt, A. C.;
MacLellan, J. G.; Thompson, C. D. Organometallics 2013, 32 (24),
7509.
(41) The authors report some dimerization of the propargylamine.
We observed no evidence of this reaction occurring.
(42) Plaquevent, J.-C.; Ravard, A. J. Organomet. Chem. 1989, 361 (3),
C51.
(6) Border, E. C.; Koutsaplis, M.; Andrews, P. C. Organometallics
2016, 35 (3), 303.
(7) Border, E. C.; Maguire, M.; MacLellan, J. G.; Andrews, P. C.
Organometallics 2017, 36 (8), 1496.
(8) Andrews, P. C.; Calleja, S. M.; Maguire, M.; Nichols, P. J. Eur. J.
Inorg. Chem. 2002, 2002 (7), 1583.
(9) Andrews, P. C.; Blair, V. L.; Koutsaplis, M.; Thompson, C. D.
Organometallics 2012, 31 (23), 8135.
(10) Flynn, M. T.; Stott, R.; Blair, V. L.; Andrews, P. C.
Organometallics 2016, 35 (16), 2707.
(11) Vessally, E.; Hosseinian, A.; Edjlali, L.; Esrafili, A. B.; M, D. Curr.
Org. Synth. 2017, 14, 557−567.
(12) Vessally, E.; Edjlali, L.; Hosseinian, A.; Bekhradnia, A.; Esrafili,
M. D. RSC Adv. 2016, 6 (55), 49730.
(13) Vessally, E. RSC Adv. 2016, 6 (22), 18619.
(14) Liu, Y. ARKIVOC 2014, 1, 1.
(15) Yamazaki, S. Chem. - Eur. J. 2008, 14 (20), 6026.
(16) Bisai, V.; Singh, V. K. Tetrahedron Lett. 2016, 57 (43), 4771.
(17) Nelson, K. G.; Larsen, C. H. Synlett 2014, 25 (19), 2681.
(18) Yoo, W.; Zhao, L.; Li, C. Aldrichimica Acta 2011, 44 (2), 43.
(19) de Armas, P.; Tejedor, D.; García-Tellado, F. Angew. Chem., Int.
Ed. 2010, 49 (6), 1013.
́ ́
(20) Bonnet-Delpon, D.; Begue, J.-P.; Crousse, B. In Fluorine-
Containing Synthons; American Chemical Society: Washington, DC,
2005; ACS Symposium Series 911, pp 24−412.
(21) Takayama, Y.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1997, 38
(48), 8351.
(22) Mizota, I.; Matsuda, Y.; Hachiya, I.; Shimizu, M. Eur. J. Org.
Chem. 2009, 2009 (24), 4073.
(23) Rezaei, H.; Marek, I.; Normant, J. F. Tetrahedron 2001, 57 (13),
2477.
(24) de Jong, R. L. P.; Brandsma, L. Synth. Commun. 1990, 20 (22),
3427.
(25) Finnegan, R. A.; McNees, R. S. J. Org. Chem. 1964, 29 (11),
3234.
(26) McCormick, B. J.; Siemer, C.; Afroz, F.; Wasson, J. R.; Eichhorn,
D. M.; Scott, B.; Shah, S.; Noffsinger, K.; Kahol, P. K. Synth. Met.
2001, 120 (1), 969.
(27) Barluenga, J.; Bayon, A. M.; Asensio, G. J. Chem. Soc., Chem.
Commun. 1983, 1109.
(28) Barluenga, J.; Bayon, A. M.; Campos, P.; Asensio, G.; Gonzalez-
Nunez, E.; Molina, Y. J. Chem. Soc., Perkin Trans. 1 1988, 1631.
(29) Priester, W.; West, R.; Chwang, T. L. J. Am. Chem. Soc. 1976, 98
(26), 8413.
(30) Barluenga, J.; Foubelo, F.; Fananas, F. J.; Yus, M. J. Chem. Soc.,
Perkin Trans. 1 1989, 553.
(31) Majumdar, K. C.; Nandi, R. K.; Ganai, S.; Taher, A. Synlett 2011,
2011 (1), 116.
(32) Zhou, Y.; Porco, J. A.; Snyder, J. K. Org. Lett. 2007, 9 (3), 393.
(33) Beccalli, E. M.; Bernasconi, A.; Borsini, E.; Broggini, G.;
Rigamonti, M.; Zecchi, G. J. Org. Chem. 2010, 75 (20), 6923.
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