Full Paper
[5]
J. A. Love, Org. Lett. 2008, 10, 3941–3944; e) L. R. Fraser, J. Bird, Q. Wu,
C. Cao, B. O. Patrick, J. A. Love, Organometallics 2007, 26, 5602–5611; f)
C. Cao, L. R. Fraser, J. A. Love, J. Am. Chem. Soc. 2005, 127, 17614–17615;
g) M. Yoshiyuki, S. Hidetake, M. Yasushi, J. Organomet. Chem. 2006, 691,
3157–3164; h) G. Kleinhans, G. Guisado-Barrios, D. C. Liles, G. Bertrand,
D. I. Bezuidenhout, Chem. Commun. 2016, 52, 3504–3507; palladium-
catalysed: i) V. P. Ananikov, N. V. Orlov, I. P. Beletskaya, V. N. Khrustalev,
M. Y. Antipin, T. V. Timofeeva, J. Am. Chem. Soc. 2007, 129, 7252–7253; j)
A. Ogawa, T. Ikeda, K. Kimura, T. Hirao, J. Am. Chem. Soc. 1999, 121,
5108–5114; k) A. Ogawa, J. Organomet. Chem. 2000, 611, 463–474; l) H.
Kuniyasu, A. Ogawa, K. Sato, I. Ryu, N. Kambe, N. Sonoda, J. Am. Chem.
Soc. 1992, 114, 5902–5903; m) E. S. Degtyareva, J. V. Burykina, A. N.
Fakhrutdinov, E. G. Gordeev, V. N. Khrustalev, V. P. Ananikov, ACS Catal.
2015, 5, 7208–7213; n) H. Ma, X. Ren, X. Zhou, C. Ma, Y. He, G. Huang,
Tetrahedron Lett. 2015, 56, 6022–6029; for metal-catalysed anti-Markov-
nikov selectivity, Rhodium-catalysed, see: o) L. D. Field, B. A. Messerle,
K. Q. Vuong, P. Turner, Dalton Trans. 2009, 3599–3614; p) S. Shoai, P.
Bichler, B. Kang, H. Buckley, J. A. Love, Organometallics 2007, 26, 5778–
5781; q) S. Burling, L. D. Field, B. A. Messerle, K. Q. Vuong, P. Turner,
Dalton Trans. 2003, 4181–4191; r) Y. Yang, R. M. Rioux, Chem. Commun.
2011, 47, 6557–6559; s) H. Zhao, J. Peng, M. Cai, Catal. Lett. 2012, 142,
138–142; t) E. R. Kiemele, M. Wathier, P. Bichler, J. A. Love, Org. Lett. 2016,
18, 492–495; palladium-catalysed: u) R. Gerber, C. M. Frech, Chem. Eur. J.
2012, 18, 8901–8905; v) A. Kondoh, H. Yorimitsu, K. Oshima, Org. Lett.
2007, 9, 1383–1385.
a) A. M. Suess, G. Lalic, Synlett 2016, 27, 1165–1174; b) M. S. Sanford,
J. T. Groves, Angew. Chem. Int. Ed. 2004, 43, 588–590; Angew. Chem. 2004,
116, 598–600; c) M. R. Uehling, R. P. Rucker, G. Lalic, J. Am. Chem. Soc.
2014, 136, 8799–8803; d) A. Dondoni, Asymmetric Catal. 2015, 2, 51–
54; e) J. J. Brunet, D. Neibecker, Catalytic Hydroamination of Unsaturated
Carbon-Carbon Bonds, in: Catalytic Heterofunctionalization (Eds.: A. Togni,
H. Grützmacher), Wiley-VCH, Weinheim, Germany, 2001, p. 91–141; f) F.
Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104–114; g) F. Alonso, I. Belets-
kaya, M. Yus, Chem. Rev. 2004, 104, 3079–3160; h) S. A. Ryken, L. L. Scha-
fer, Acc. Chem. Res. 2015, 48, 2576–2586.
a) R. Ekkebus, S. I. van Kasteren, Y. Kulathu, A. Scholten, I. Berlin, P. P.
Geurink, A. de Jong, S. Goerdayal, J. Neefjes, A. J. R. Heck, D. Komander,
H. Ovaa, J. Am. Chem. Soc. 2013, 135, 2867–2870; b) H. W. Lam, P. A.
Cooke, G. Pattenden, W. M. Bandaranayake, W. A. Wickramasinghe, J.
Chem. Soc. Perkin Trans. 1 1999, 847–848; c) J. J. Li, E. J. Corey, Total
Synthesis of Natural Products, Springer-Verlag, Berlin, Heidelberg, 2012;
d) E. V. Prusov, Angew. Chem. Int. Ed. 2014, 53, 6037; Angew. Chem. 2014,
126, 6149; e) E. Marcantoni, M. Massaccesi, M. Petrini, G. Bartoli, M. C.
Bellucci, M. Bosco, L. Sambri, J. Org. Chem. 2000, 65, 4553–4559; f) Y.
Tian, J. Li, H. Zhao, X. Zeng, D. Wang, Q. Liu, X. Niu, X. Huang, N. Xu, Z.
Li, Chem. Sci. 2016, 7, 3325–3330.
a) K. Nakabayashi, A. Matsumura, Y. Abiko, H. Mori, Macromolecules 2016,
49, 1616–1629; b) Y. Abiko, A. Matsumura, K. Nakabayashi, H. Mori, React.
Funct. Polym. 2015, 93, 170–177; c) M. M. Bassaco, M. Monçalves, F. Rin-
aldi, T. S. Kaufman, C. da C. Silveira, J. Photochem. Photobiol. A 2014, 290,
1–10; d) R. Pötzsch, B. C. Stahl, H. Komber, C. J. Hawker, B. I. Voit, Polym.
Chem. 2014, 5, 2911–2921; e) M. L. Conte, S. Staderini, A. Marra, M. San-
chez-Navarro, B. G. Davis, A. Dondoni, Chem. Commun. 2011, 47, 11086–
11088; f) K. Nakabayashi, Y. Abiko, H. Mori, Macromolecules 2013, 46,
5998–6012; g) A. B. Lowe, C. E. Hoyle, C. N. Bowman, J. Mater. Chem.
2010, 20, 4745–4750; h) H. Lee, H. Kim, T. J. Choi, H. W. Park, J. Y. Chang,
Chem. Commun. 2015, 51, 9805–9808.
[6]
[7]
[12]
For metal-catalysed anti-Markovnikov selectivity, Copper-catalysed, see:
a) N. R. Siti, Y. Y. Jackie, Z. Yugen, Org. Lett. 2012, 14, 1780–1783; b) Y.
Yang, R. M. Rioux, Green Chem. 2014, 16, 3916–3925; c) I. G. Trostyan-
skaya, I. P. Beletskaya, Synlett 2012, 23, 535–540; Gold-catalysed: d) A.
Corma, C. González-Arellano, M. Iglesias, F. Sánchez, Appl. Catal. A 2010,
375, 49–54; e) S. Biswas, C. Dahlstrand, R. A. Watile, M. Kalek, F. Himo,
J. S. M. Samec, Chem. Eur. J. 2013, 19, 17939–17950.
[13]
[14]
For actinide-catalysed Markovnikov selectivity, see: a) C. J. Weiss, S. D.
Wobser, T. J. Marks, J. Am. Chem. Soc. 2009, 131, 2062–2063; b) C. J.
Weiss, T. J. Marks, Dalton Trans. 2010, 39, 6576–6588.
[8]
a) J. C. Lo, J. Gui, Y. Yabe, C.-M. Pan, P. S. Baran, Nature 2014, 516, 343–
348; b) Q. Li, T. Dong, X. Liu, X. Lei, J. Am. Chem. Soc. 2013, 135, 4996–
4999; c) S. F. Malysheva, A. V. Artem'ev, N. K. Gusarova, N. A. Belogorlova,
A. I. Albanov, C. W. Liu, B. A. Trofimov, Beilstein J. Org. Chem. 2015, 11,
1985–1990; d) M.-G. Braun, S. Z. Zard, Org. Lett. 2011, 13, 776–777; e) B.-
T. Gröbel, D. Seebach, Synthesis 1977, 357–402; f) T. Hanamoto, R. Anno,
K. Yamada, K. Ryu, R. Maeda, K. Aoi, H. Furuno, Tetrahedron 2009, 65,
2757–2765; g) J. D. Webb, D. J. Harrison, D. W. Norman, J. M. Blacquiere,
C. M. Vogels, A. Decken, C. G. Bates, D. Venkataraman, R. T. Baker, S. A.
Westcott, J. Mol. Catal. A 2007, 275, 91–100; h) Y. Cui, P. E. Floreancig,
Org. Lett. 2012, 14, 1720–1723; i) K. Miyamoto, M. Hirobe, M. Uchiyama,
M. Ochiai, Chem. Commun. 2015, 51, 7962–7965; j) G. Liu, L. Kong, J.
Shen, G. Zhu, Org. Biomol. Chem. 2014, 12, 2310–2321; k) O. Boutureira,
M. I. Matheu, Y. Díaz, S. Castillón, RSC Adv. 2014, 4, 19794–19799.
a) P. Johannesson, G. Lindeberg, A. Johansson, G. V. Nikiforovich, A. Go-
goll, B. Synnergren, M. L. Grèves, F. Nyberg, A. Karlén, A. Hallberg, J. Med.
Chem. 2002, 45, 1767–1777; b) R. Budriesi, B. Cosimelli, P. Ioan, M. P.
Ugenti, E. Carosati, M. Frosini, F. Fusi, R. Spisani, S. Saponara, G. Cruciani,
E. Novellino, D. Spinelli, A. Chiarini, J. Med. Chem. 2009, 52, 2352–2362;
c) V. R. Pallela, M. R. Mallireddigari, S. C. Cosenza, B. Akula, D. R. C. V.
Subbaiah, E. P. Reddy, M. V. R. Reddy, Org. Biomol. Chem. 2013, 11, 1964–
1977.
a) R. Castarlenas, A. Di Giuseppe, J. J. Pérez-Torrente, L. A. Oro, Angew.
Chem. Int. Ed. 2013, 52, 211–222; Angew. Chem. 2013, 125, 223–234; b)
V. P. Ananikov, K. A. Gayduk, N. V. Orlov, I. P. Beletskaya, V. N. Khrustalev,
M. Y. Antipin, Chem. Eur. J. 2010, 16, 2063–2071; c) M. Beller, J. Seayad,
A. Tillack, H. Jiao, Angew. Chem. Int. Ed. 2004, 43, 3368–3398; Angew.
Chem. 2004, 116, 3448–3479; d) X. H. Zhang, K. T. Wang, RSC Adv. 2015,
5, 34439–34446; e) V. Ritleng, M. Henrion, M. J. Chetcuti, ACS Catal. 2016,
6, 890–906; f) A. Dondoni, A. Marra, Eur. J. Org. Chem. 2014, 3955–3969;
g) X. H. Zhang, Z. Y. Geng, K. T. Wang, S. S. Li, J. Mol. Model. 2014, 20,
2409–2419.
For main-group-element-catalysed anti-Markovnikov selectivity, see: a)
M. S. Silva, R. G. Lara, J. M. Marczewski, R. G. Jacob, E. J. Lenardão, G.
Perin, Tetrahedron Lett. 2008, 49, 1927–1930; b) E. J. Lenardão, M. S. Silva,
R. G. Lara, J. M. Marczewski, M. Sachini, R. G. Jacob, D. Alves, G. Perin,
ARKIVOC (Gainesville, FL, U.S.) 2011, 2, 272–282; c) J. L. Eder, K. S. Liane,
M. B. Angelita, P. Gelson, Curr. Green Chem. 2016, 3, 4–17; for indium-
catalysed anti-Markovnikov selectivity, see: d) N. Rajesh, D. Prajapati, RSC
Adv. 2014, 4, 32108–32112.
For nickel-catalysed Markovnikov selectivity, see: a) D. A. Malyshev, N. M.
Scott, N. Marion, E. D. Stevens, V. P. Ananikov, I. P. Beletskaya, S. P. Nolan,
Organometallics 2006, 25, 4462–4470; b) V. P. Ananikov, N. V. Orlov, I. P.
Beletskaya, Organometallics 2006, 25, 1970–1977; c) V. P. Ananikov, D. A.
Malyshev, I. P. Beletskaya, G. G. Aleksandrov, I. L. Eremenko, Adv. Synth.
Catal. 2005, 347, 1993–2001; for zirconium-catalysed Markovnikov se-
lectivity, see: d) C. J. Weiss, T. J. Marks, J. Am. Chem. Soc. 2010, 132,
10533–10546.
a) C.-J. Li, T. H. Chan, Comprehensive Organic Reactions in Aqueous Media,
2nd ed., Wiley, New York, 2007; b) R. Sheldon, I. Arends, U. Hanefeld,
Green Chemistry and Catalysis, Wiley-VCH, Weinheim, Germany, 2007; c)
H. D. Velazquez, F. Verpoort, Chem. Soc. Rev. 2012, 41, 7032–7060; d) M.
Lombardo, C. Trombini, Curr. Opin. Drug Discov. Devel. 2010, 13, 717–
732; e) A. A. Marianou, C. M. Michailof, A. Pineda, E. F. Iliopoulou, K. S.
Triantafyllidis, A. A. Lappas, ChemCatChem 2016, 8, 1100–1110; f) B. Cor-
nils, W. A. Herrmann (Eds.), Aqueous-Phase Organometallic Catalysis: Con-
cepts and Applications, 2nd ed., Wiley-VCH, Weinheim, Germany, 2004.
S. Kankala, S. Nerella, R. Vadde, C. S. Vasam, RSC Adv. 2013, 3, 23582–
23588.
a) C. Long, J. Phys. Chem. A 2012, 116, 6845–6850; b) P. J. Dyson, Dalton
Trans. 2003, 2964–2974; c) C. P. Casey, G. A. Bikzhanova, Q. Cui, I. A.
Guzei, J. Am. Chem. Soc. 2005, 127, 14062–14071; d) S. Müller-Becker, W.
Frank, J. Schneider, Z. Anorg. Allg. Chem. 1993, 619, 1073–1082; e) R.
Makhoul, J. A. Shaw-Taberlet, H. Sahnoune, V. Dorcet, S. Kahlal, J.-F. Halet,
J.-R. Hamon, C. Lapinte, Organometallics 2014, 33, 6023–6032; f) R. S.
Koefod, K. R. Mann, J. Am. Chem. Soc. 1990, 112, 7287–7293; g) R. L.
Lord, C. K. Schauer, F. A. Schultz, M.-H. Baik, J. Am. Chem. Soc. 2011, 133,
[15]
[16]
[9]
[10]
[17]
[18]
[11]
For metal-catalysed Markovnikov selectivity, Ruthenium-catalysed, see:
a) U. Koelle, C. Rietmann, J. Tjoe, T. Wagner, U. Englert, Organometallics
1995, 14, 703–713; rhodium-catalysed: b) A. Di Giuseppe, R. Castarlenas,
J. J. Pérez-Torrente, M. Crucianelli, V. Polo, R. Sancho, F. J. Lahoz, L. A. Oro,
J. Am. Chem. Soc. 2012, 134, 8171–8183; c) J. Yang, A. Sabarre, L. R. Fraser,
B. O. Patrick, J. A. Love, J. Org. Chem. 2009, 74, 182–187; d) A. Sabarre,
Eur. J. Org. Chem. 0000, 0–0
7
© 0000 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim