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ChemComm
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DOI: 10.1039/C5CC08717A
COMMUNICATION
Journal Name
14 C. J. O’Brien, E. A. B. Kantchev, C. Valente, N. Hadei, G. A. Chass,
A. Lough, A. Hopkinson and M. G. Organ, Chem. ‒ Eur. J., 2006,
12, 4743.
15 Selected reviews on tzNHCs: (a) O. Schuster, L. Yang, H. G.
Raubenheimer and M. Albrecht, Chem. Rev., 2009, 109, 3445;
carbene palladium reactive species are involved in two
connected palladium catalytic cycles.
Financial support from the Ministry of Education, Science
and Sport, Republic of Slovenia, the Slovenian Research
Agency (Grant P1-0230; Postdoctoral Grant to M.G. (430-
168/2013/114), and Grant P1-0175) is acknowledged. This
work was partially supported through the infrastructure of the
EN-FIST Centre of Excellence, Ljubljana, Slovenia.
Dedicated to Dr. Maja Osmak on the occasion of her 65th
birthday.
(b) J. D. Crowley, A. Lee and K. J. Kilpin, Aust. J. Chem., 2011, 64
1118; (c) D. J. Nelson and S. P. Nolan, Chem. Soc. Rev., 2013, 42
6723; (d) R. H. Crabtree, Coord. Chem. Rev., 2013, 257, 755; (e)
B. Schulze, U. S. Schubert, Chem. Soc. Rev., 2014, 43, 2522.
16 (a) W. A. Herrmann, Angew. Chem., Int. Ed., 2002, 41, 1290; (b)
M. Melaimi, M. Soleilhavoup and G. Bertrand, Angew. Chem.,
,
,
Int. Ed., 2010, 49, 8810; (c) X.-F. Wu, H. Neumann and M. Beller,
Chem. Soc. Rev., 2011, 40, 4986; (d) S. Inomata, H. Hiroki, T.
Terashima, K. Ogata and S. Fukuzawa, Tetrahedron, 2011, 67
,
7263; (e) K. F. Donnelly, A. Petronilho and M. Albrecht, Chem.
Commun., 2013, 49, 1145.
17 D. Canseco-Gonzalez, A. Gniewek, M. Szulmanowicz, H. Müller-
Notes and references
1
2
3
A. J. Arduengo, R. L. Harlow and M. J. Kline, J. Am. Chem. Soc.,
1991, 113, 361.
W. A. Herrmann, M. Elison, J. Fischer, C. Köcher and G. R. J.
Artus, Angew. Chem., Int. Ed. Engl., 1995, 34, 2371.
R. Jackstell, M. G. Andreu, A. Frisch, K. Selvakumar, A. Zapf, H.
Klein, A. Spannenberg, D. Röttger, O. Briel, R. Karch and M.
Beller, Angew. Chem., Int. Ed., 2002, 41, 986.
Bunz, A. M. Trzeciak and M. Albrecht, Chem. ‒ Eur. J., 2012, 18
6055.
,
18 J. Huang, J.-T. Hong and S. H. Hong, Eur. J. Org. Chem., 2012,
6630.
19 (a) K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett.,
1975, 16, 4467; (b) K. Sonogashira, in Metal Catalyzed Cross-
Coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH,
Weinheim, 1998, 203–229; (c) H. Doucet and J.-C. Hierso,
Angew. Chem., Int. Ed., 2007, 46, 834; (d) M. Lamblin, L. Nassar-
Hardy, J.-C. Hierso, E. Fouquet and F.-X. Felpin, Adv. Synth.
Catal., 2010, 352, 33; (e) M. Bakherad, Appl. Organometal.
Chem., 2013, 27, 125; (f) A. M. Thomas, A. Sujatha and G.
4
5
6
7
8
9
L. R. Titcomb, S. Caddick, F. G. N. Cloke, D. J. Wilson and D.
McKerrecher, Chem. Commun., 2001, 1388.
M. S. Viciu, R. F. Germaneau, O. Navarro-Fernandez, E. D.
Stevens and S. P. Nolan, Organometallics, 2002, 21, 5470.
V. César, S. Bellemin-Laponnaz and L. H. Gade, Organometallics,
2002, 21, 5204.
D. R. Jensen, M. J. Schultz, J. A. Mueller and M. S. Sigman,
Angew. Chem., Int. Ed., 2003, 42, 3810.
P. Mathew, A. Neels and M. Albrecht, J. Am. Chem. Soc., 2008,
130, 13534.
(a) T. Karthikeyan and S. Sankararaman, Tetrahedron Lett., 2009,
50, 5834; (b) T. Nakamura, K. Ogata and S. Fukuzawa, Chem.
Lett., 2010, 39, 920; (c) S. Hohloch, W. Frey, C.-Y. Suc and B.
Sarkar, Dalton Trans., 2013, 42, 11355; (d) M. Górna, M. S.
Szulmanowicz, A. Gniewek, W. Tylus and A. M. Trzeciak, J.
Organomet. Chem., 2015, 785, 92.
Anilkumar, RSC Adv., 2014,
Lin, C. Vargas and R. Luque, Org. Biomol. Chem., 2014, 12, 10.
20 D. Wang and S. Gao, Org. Chem. Front., 2014, , 556.
4, 21688; (g) R. A. D. Arancon, C. S. K.
1
21 R. Chinchilla and C. Nájera, Chem. Rev., 2007, 107, 874.
22 (a) A. O. King and N. Yasuda, Top. Organomet. Chem. 2004,
205; (b) C. Torborg and M. Beller, Adv. Synth. Catal., 2009, 351
6,
,
3027.
23 (a) H. D. Velazquez and F. Verpoort, Chem. Soc. Rev., 2012, 41
,
7032; (b) Metal-Catalyzed Reactions in Water, ed. P. Dixneuf and
V. Cadierno, Wiley-VCH, Weinheim, 2013; (c) E. Levin, E. Ivry, C.
E. Diesendruck and N. G. Lemcoff, Chem. Rev., 2015, 115, 4607.
24 (a) L. Yang, P. Guan, P. He, Q. Chen, C. Cao, Y. Peng, Z. Shi, G.
Pang and Y. Shi, Dalton Trans., 2012, 41, 5020; (b) A. Kumar and
P. Ghosh, Eur. J. Inorg. Chem., 2012, 3955 and references
therein; (c) C. W. D. Gallop, M.-T. Chen and O. Navarro, Org.
Lett., 2014, 16, 3724.
25 A. Bolje and J. Košmrlj, Org. Lett., 2013, 15, 5084.
26 E. C. Keske, O. V. Zenkina, R. Wang and C. M. Crudden,
Organometallics, 2012, 31, 6215.
27 F. F. Wagner and D. L. Comins, J. Org. Chem., 2006, 71, 8673.
28 R. H. Crabtree, Chem. Rev., 2012, 112, 1536.
29 M. S. Szulmanowicz, A. Gniewek, W. Gil and A. M. Trzeciak,
10 Selected reviews on N-heterocyclic carbenes: (a) J. C. Garrison
and W. J. Youngs, Chem. Rev., 2005, 105, 3978; (b) N. Marion, S.
Díez-González and S. P. Nolan, Angew. Chem., Int. Ed., 2007, 46
2988; (c) F. A. Glorius, Top. Organomet. Chem., 2007, 21, 1; (d)
E. A. B. Kantchev, C. J. O’Brien and M. G. Organ, Angew. Chem.,
Int. Ed., 2007, 46, 2768; (e) O. Kühl, Coord Chem Rev., 2009, 253
2481; (f) M. C. Jahnke and F. E. Hahn, Top. Organomet. Chem.,
2010, 30, 95; (g) S. Budagumpi, R. A. Haque and A. W. Salman,
Coord. Chem. Rev., 2012, 256, 1787; (h) M. Fèvre, J. Pinaud, Y.
Gnanou, J. Vignolle and D. Taton, Chem. Soc. Rev., 2013, 42
2142; (i) N-Heterocyclic Carbenes. Effective Tools for
Organometallic Synthesis, ed. S. P. Nolan, Wiley-VCH, Weinheim,
2014; (j) T. A. Schaub and M. Kivala, in Metal-Catalyzed Cross-
Coupling Reactions and More, ed. A. de Meijere, S. Bräse and M.
Oestreich, Wiley-VCH, Weinheim, 2014, 665–762; (k) D. M.
Flanigan, F. Romanov-Michailidis, N. A. White and T. Rovis,
Chem. Rev., 2015, 115, 9307.
,
,
,
ChemCatChem, 2013, 5, 1152.
30 (a) D. Schröder, Acc. Chem. Res., 2012, 45, 1521; (b) K. L. Vikse,
Z. Ahmadi and J. S. McIndoe, Coord. Chem. Rev., 2014, 279, 96.
31 J. Pytkowicz, S. Roland, P. Mangeney, G. Meyer and A. Jutand, J.
Organomet. Chem., 2003, 678, 166.
11 (a) A. A. D. Tulloch, A. A. Danopoulos, R. P. Tooze, S. M.
Cafferkey, S. Kleinhenz and M. B. Hursthouse, Chem. Commun.,
2000, 1247–1248; (b) D. S. McGuinness and K. J. Cavell,
Organometallics, 2000, 19, 741.
12 A. A. D. Tulloch, A. A. Danopoulos, G. J. Tizzard, S. J. Coles, M. B.
Hursthouse, R. S. Hay-Motherwell and W. B. Motherwell, Chem.
Commun., 2001, 1270.
13 V. Khlebnikov, A. Meduri, H. Mueller-Bunz, T. Montini, P.
Fornasiero, E. Zangrando, B. Milani and M. Albrecht,
Organometallics, 2012, 31, 976.
32 A. K. K. Lewis, S. Caddick, F. G. N. Cloke, N. C. Billingham, P. B.
Hitchcock and J. Leonard, J. Am. Chem. Soc., 2003, 125, 10066.
33 (a) U. Christmann and R. Vilar, Angew. Chem., Int. Ed., 2005, 44
366; (b) A. Jutand, Chem. Rev., 2008, 108, 2300; (c) A. Jutand, J.
Pytkowicz, S. Roland and P. Mangeney, Pure Appl. Chem., 2010,
82, 1393.
34 G. P. McGlacken and I. J. S. Fairlamb, Eur. J. Org. Chem., 2009,
4011.
,
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