ChemComm
Page 4 of 5
DOI: 10.1039/C5CC00123D
2006, 13, 3016–3020. (c) E. Trogu, L. Cecchi, F. De Sarlo, L.
Guideri, F. Ponticelli and F. Machetti, Eur. J. Org. Chem., 2009, 34
5971–5978.
75
6
7
R. Ballini, G. Bosica and D. Fiorini, Tetrahedron, 2003, 59, 1143–
1145.
5
10
15
20
(a) G. Rosini, R. Ballini and V. Zanotti, Synthesis, 1983, 2, 137–139.
(b) R. Ballini and G. Bosica, J. Org. Chem., 1994, 59, 5466–5467. (c)
G. Rosini and R. Ballini, Synthesis, 1983, 3 228–230.
(a) A. R. Butler and E. H. Brown, Arkivoc, 2002, 3, 166–171. (b) H.
H. Nguyen and M. J. Kurth, Org. Lett., 2013, 15, 362–365.
9
10 G. Rosini and R. Ballini, Synthesis, 1988, 11, 833–847.
11 (a) O. Soltani, M. A. Ariger, H. VazquezꢀVilla and E. M. Carreira,
Org. Lett., 2010, 12, 2893–2895. (b) V. N. G. Lindsay, C. Nicolas
and A. B. Charette, J. Am. Chem. Soc., 2011, 133, 8972–8981. (c) A.
Riahi, M. Shkoor, R. A. Khera, H. Reinke and P. Langer,
Tetrahedron Lett., 2009, 50, 3017–3019. (d) H. H. Nguyen and M. J.
Kurth, Org. Lett., 2013, 15, 362–365. (e) M. Shaikh, M. Satanami
and K. V. S. Ranganath, Catal. Commun., 2014, 54, 91–93.
12 Other less applied approaches include olefin nitration or oxidation
and azide oxidation: (a) R. Rathore, Z. Lin and J. K. Kochi,
Tetrahedron Lett., 1993, 34, 1859–1862. (b) M. V. R. Reddy, R.
Kumareswaran and Y. D. Vankar, Tetrahedron Lett., 1995, 36,
7149–7152. (c) M. Carmeli and S. Rozen, J. Org. Chem., 2006, 71,
4585–4589.
25 13 (a) S. Korsager, D. U. Nielsen, R. H. Taaning and T. Skrydstrup,
Angew. Chem. Int. Edit., 2013, 52, 9763–9766. (b) Z. Lian, S. D.
Friis and T. Skrydstrup, Angew. Chem., Int. Ed. 2014, 53, 9582–
9586. (c) T. M. Gøgsig, R. H. Taaning, A. T. Lindhardt and T.
Skrydstrup, Angew. Chem. Int. Edit., 2012, 51, 798–801. (d) D. U.
30
35
40
45
50
55
60
65
Nielsen, C. Lescot, T. M. Gogsig, A. T. Lindhardt and T. Skrydstrup,
Chem.ꢀEur. J., 2013, 19, 17926–17938. (e) J. Schranck, A. Tlili, P.
G. Alsabeh, H. Neumann, M. Stradiotto and M. Beller, Chem.ꢀEur.
J., 2013, 19, 12624–12628. (f) J. Schranck, M. Burhardt, C.
Bornschein, H. Neumann, T. Skrydstrup and M. Beller, Chem.ꢀEur.
J., 2014, 20, 9534–9538.
14 A. R. Katritzky, A. A. A. AbdelꢀFattah, A. V. Gromova, R. Witek,
and P. J. Steel, J. Org. Chem. 2005, 70, 9211–9214.
15 (a) P. Hermange, A. T. Lindhardt, R. H. Taaning, K. Bjerglund, D.
Lupp and T. Skrydstrup, J. Am. Chem. Soc., 2011, 133, 6061–6071.
The carbon monoxide may also be generated from other precursors:
(b) S. D. Friis, R. H. Taaning, A. T. Lindhardt and T. Skrydstrup, J.
Am. Chem. Soc. 2011, 133, 18114–18117. (c) P. Nordeman, L. R.
Odell and M. Larhed, J. Org. Chem. 2012, 77, 11393–11398.
16 For selected recent work on carbonylation chemistry, see: (a) H. Li,
H. Neumann, M. Beller and X.ꢀF. Wu, Angew. Chem. Int. Ed. 2014,
53, 3183–3186. (b) X. Fang, H. Li, R. Jackstell, and M. Beller, J. Am.
Chem. Soc., 2014, 136, 16039–16043. (c) Lian, S. D. Friis, A. T.
Lindhardt and T. Skrydstrup, Synlett, 2014, 25, 1241–1245. (d) M.
Bjerglund, T. Skrydstrup and G. A. Molander, Org. Lett., 2014, 16,
1888–1891. (e) J. S. Quesnel and B. A. Arndtsen, J. Am. Chem. Soc.,
2013, 135, 16841–16844. (f) Xu and H. Alper, J. Am. Chem. Soc.,
2014, 136, 16970–16973. (g) Y. Hoshimot, T. Ohata, Y. Sasaoka, M.
Ohashi, and S. Ogoshi, J. Am. Chem. Soc., 2014, 136, 15877−15880.
17 (a) M. Iizuka and Y. Kondo, Chem. Commun., 2006, 16, 1739–1741.
(b) Z. Lian, S. D. Friis and T. Skrydstrup, Chem. Commun., 2014,
DOI: 10.1039/c4cc09303h. (c) H. Neumann, A. Brennführer, and M.
Beller, Chem. Eur. J. 2008, 14, 3645–3652.
18 (a) J. R. Martinelli, D. A. Watson, D. M. M. Freckmann, T. E. Barder
and S. L. Buchwald, J. Org. Chem. 2008, 73, 7102–7107. (b) S. D.
Friis, T. L. Andersen and T. Skrydstrup, Org. Lett. 2013, 15, 1378–
1381.
19 (a) E. Vitaku, D. T. Smith and J. T. Njardarson, J. Med. Chem. 2014,
ASAP, DOI: 10.1021/jm501100b. (b) S. D. Friis, T. Skrydstrup and
S. L. Buchwald, Org. Lett. 2014, 16, 4296–4299. (c) M. A. Düfert, K.
L. Billingsley, S. L. Buchwald, J. Am. Chem. Soc. 2013, 135, 12877–
12885. (d) M. W. Hooper, J. F. Hartwig, Organometallics, 2003, 22,
3394–3403.
20 L. Cecchi, F. De Sarlo and F. Machetti, Eur. J. Org. Chem., 2006, 21,
4852–4860.
70 21 (a) R. Tamura, D. Oda and H. Kurokawa, Tetrahedron Lett., 1986,
27, 5759–5762. (b) P. C. Tang, Y. Su, L. Zhang and L. Xiao, 2010,
Pyrrolo [3,2ꢀc] pyridineꢀ4ꢀone 2ꢀindolinone protein kinase inhibitors,
US Patent: US 20100004239 A1.
4
|
Journal Name, [year], [vol], 00–00
This journal is © The Royal Society of Chemistry [year]