10.1002/cctc.201600868
ChemCatChem
Paulus, H. G. Schmitt (A. G. Bayer), Ger. Offen. DE
3526789, 1987 (Chem. Abstr. 1987, 106, 98104).
N. Shimizu, J. Org. Chem. 1984, 49, 3429-3432; f) R.
H. Boutin, H. Rapoport, J. Org. Chem. 1986, 51,
5320-5327; g) T. D. Aicher, Y. Kishi, Tetrahedron
Lett. 1987, 28, 3463-3466; h) Y. Kishi, Pure Appl.
Chem. 1992, 64, 343-350; i) K. C. Nicolaou, A. Liu,
Z. Zeng, S. McComb, J. Am. Chem. Soc. 1992, 114,
9279-9282; j) T. Mandai, T. Matsumoto, M. Kawada,
J. Tsuji, J. Org. Chem. 1992, 57, 6090-6092; k) J. B.
Nerenberg, D. T. Hung, P. K. Somers, S. L. Schreiber,
J. Am. Chem. Soc. 1993, 115, 12621-12622; l) L. M.
Antunes, M. G. Organ, Tetrahedron Lett. 2003, 44,
6805-6808; m) J. Picard, N. Lubin-Germain, J. Uziel,
J. Augé, Synthesis, 2006, 6, 979-982; n) N. Joubert, F.
Amblard, K. L. Rapp, R. F. Schinazi, L. A.
Agrofoglio, Tetrahedron, 2008, 64, 4444-4452; o) S.
Dei, T. Shimogaki, A. Matsumoto, Macromolecules,
2008, 41, 6055-6065; p) D. A. Barancelli, A. C.
Mantovani, C. Jesse, C. W. Nogueira, G. Zeni, J. Nat.
Prod. 2009, 72, 857-860; q) R. C. Hoye, G. L.
Anderson, S. G. Brown, E. E. Schultz, J. Org. Chem.
2010, 75, 7400-7403; r) K. Mori, Tetrahedron, 2012,
68, 1936-1946; s) M. Ruetz, R. Salchner, K. Wurst, S.
Fedosov, B. Kräutler, Angew. Chem. 2013, 125,
11617-11620; Angew.Chem. Int. Ed. 2013, 52,
11406-11409; t) K. Okamoto, M. Watanabe, N.
Sakata, M. Murai, K. Ohe, Org. Lett. 2013, 15, 5810-
5813.
[3] For selected examples about coupling reactions using
1-iodoalkynes, see: a) P. L. Southwick, J. R. Kirchner,
J. Org. Chem. 1962, 27, 3305-3308; b) K. Takai, T.
Kuroda, S. Nakatsukasa, K. Oshima, H. Nozaki,
Tetrahedron Lett. 1985, 26, 5585-5588; c) R.
Takeuchi, Y. Tsuji, M. Fujita, T. Kondo, Y.
Watanabe, J. Org. Chem. 1989, 54, 1831-1836; d) J.
Barluenga, J. M. González, I. Llorente, P. J. Campos,
Angew. Chem. 1993, 105, 928-929; Angew. Chem. Int.
Ed. 1993, 32, 893-894; e) M. H. Nantz, D. K. Moss, J.
D. Spence, M. M. Olmstead, Angew. Chem. 1998,
110, 476-479; Angew .Chem. Int. Ed. 1998, 37, 470-
473; f) S. Yamanoi, T. Matsumoto, K. Suzuki,
Tetrahedron Lett.1999, 40, 2793-2796; g) M.
Kunishima, D. Nakata, S. Tanaka, K. Hioki, S. Tani,
Tetrahedron, 2000, 56, 9927-9935; h) M. V. Russo, C.
Lo Sterzo, P. Franceschini, G. Biagini, A. Furlani, J.
Organomet. Chem. 2001, 619, 49-61; i) Y. Y. Ku, T.
Grieme, P. Sharma, Y.-M. Pu, P. Raje, H. Morton, S.
King, Org. Lett. 2001, 3, 4185-4187; j) S. V. Damle,
D. Seomoon, P. H. Lee, J. Org. Chem. 2003, 68,
7085-7087; k) A. S. K. Hashmi, R. Döpp, C.
Lothschütz, M. Rudolph, D. Riedel, F. Rominger,
Adv. Synth. Catal. 2010, 352, 1307-1314; l) D. L.
Usanov, H. Yamamoto, J. Am. Chem. Soc. 2011, 133,
1286-1289; m) H. Liu, C. Chen, L. Wang, X. Tong,
Org. Lett. 2011, 13, 5072-5075; n) M. Zhu, M. Ning,
W. Fu, C. Xu, G. Zou, Bull. Korean. Chem. Soc. 2012,
33, 1325-1328; o) S. Mader, L. Molinari, M. Rudolph,
F. Rominger, A. S. K. Hashmi, Chem. Eur. J. 2015,
21, 3910-3913.
[7] For some examples using this traditional approach,
see: a) T. H. Vaughn, J. A. Nieuwland, J. Am. Chem.
Soc. 1932, 54, 787-791; b) T. H. Vaughn, J. A.
Nieuwland, J. Am. Chem. Soc. 1933, 55, 2150-2153;
c) A. F. Kluge, K. G. Untch, J. H. Fried, J. Am. Chem.
Soc. 1972, 94, 9256-9258; d) M. Bassetti, B. Floris, G.
Illuminati, Organometallics, 1985, 4, 617-623; e) L.
Camici, P. Dembech, A. Ricci, G. Seconi, M. Taddei,
Tetrahedron, 1988, 44, 4197-4206; f) J. E. A. Luithle,
J. Pietruszka, Eur. J. Org. Chem. 2000, 2557-2562; g)
H. A. Stefani, R. Cella, F. A. Dörr, C.M. de Pereira, F.
P. Gomes, G. Zeni, Tetrahedron Lett. 2005, 46, 2001-
2003; h) G.-W. He, F.-W. Liu, X.-H. Xu, Chin. J.
Org. Chem. 2007, 27, 663-665; i) L.-G. Meng, P.-J.
Cai, Q.-X. Guo, S. Xue, Synth. Commun. 2008, 38,
225-231.
[4] For selected examples about alkyne addition reactions
using 1-iodoalkynes, see: a) G. Zweifel, H.
Arzoumanian, J. Am. Chem. Soc. 1967, 89, 5086-
5088; b) W. Xu, W.-Y. Chen, J. Org. Chem. 2002, 67,
9421-9427; c) J. E. Hein, J. C. Tripp, L. B. Krasnova,
B. Sharpless, V. V. Fokin, Angew. Chem. 2009, 121,
8162-8165; Angew. Chem. Int. Ed. 2009, 48, 8018-
8021; d) C. Recsei, C. S. P. McErlean, Tetrahedron:
Asymmetry, 2010, 21, 149-152; e) J. A. Crossley, D.
L. Browne, J. Org. Chem. 2010, 75, 5414-5416; f) M.
Juríček, K. Stout, P. H. J. Kouwer, A. E. Rowan, Org.
Lett. 2011, 13, 3494-3497; g) D. Fu, J. Zhang, S. Cao,
J. Fluorine Chem. 2013, 156, 170-176; h) Y. Gao, M.
Yin, W. Wu, H. Huang, H. Jiang, Adv. Synth. Catal.
2013, 355, 2263-2273; i) A. H. Banday, V. J. Hruby,
Synlett, 2014, 25, 2463-2466.
[8] T. Nishikawa, S. Shibaya, S. Hosokowa, M. Isobe,
Synlett, 1994, 485-486.
[9] a) G. W. Kabalka, A. R. Mereddy, Tetrahedron Lett.
2004, 45, 1417-1419; b) G. W. Kabalka, A. R.
Mereddy, J. Labelled Comp. Radiopharm. 2005, 48,
359-362.
[5] W. Wu, H. Jiang, Acc. Chem. Res. 2014, 47, 2483-
[10] a) M. J. Cohen, E. J. McNelis, J. Org. Chem. 1984,
49, 515-518; b) D. Naskar, S. Roy, J. Org.Chem.
1999, 64, 6896-6897.
2504.
[6] For some examples of the synthesis of useful
chemicals using 1-iodoalkynes as intermediates, see:
a) C. Burgess, G. Cooley, P. Feather, V. Petrow,
Tetrahedron, 1967, 23, 4111-4116; b) D. W. Knight,
G. Pattenden, J. Chem. Soc. Perkin Trans. 1975, 641-
644; c) C. Lüthy, P. Konstantin, K. G. Untch, J. Am.
Chem. Soc. 1978, 100, 6211-6217; d) R. Rossi, A.
Carpita, Tetrahedron, 1983, 39, 287-290; e) S.
Nishida, M. Murakami, T. Mizuno, T. Tsuji, H. Oda,
[11] For other examples of alkyne derivatives, see: a) P. J.
Stang, B. W. Surber, J. Am. Chem. Soc. 1985, 107,
1452-1453; b) N. Krause, D. Seebach, Chem. Ber.
1987, 120, 1845-1851; c) M. Ochiai, K. Uemura, Y.
Masaki, J. Am. Chem. Soc. 1993, 115, 2528-2529; d)
P. Michel, A. Rassat, Tetrahedron Lett. 1999, 40,
8579-8581; e) H. Lahrache, S. Robin, G. Rousseau,
Tetrahedron Lett. 2005, 46, 1635-1637.
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