10.1002/ejoc.202001328
European Journal of Organic Chemistry
COMMUNICATION
[16] B. Yu, Y. Zhao, H. Zhang, J. Xu, L. Hao, X. Gao, Z. Liu, Chem. Commun.
2014, 50, 2330.
The Schlenk tube was stirred at room temperature in case of iodo
and triflates, and at 60 °C for bromo derivatives. The reaction
mixture was diluted with dichloromethane (5 mL) and filtered
through celite® bed. The organic layer was concentrated under
reduced pressure. The residue was purified through silica gel (230
- 400 mesh) column chromatography using ethyl acetate in
petroleum ether.
[17] G. Sun, X. Lv, Y. Zhang, M. Lei, L. Hu, Org. Lett. 2017, 19, 4235.
[18] a) S. Klaus, H. Neumann, A. Zapf, D. Strubing, S. Huber, J. Almena, T.
Riermeier, P. Gross, M. Sarich, W-R. Krahnert, K. Rossen, M. Beller,
Angew. Chem., Int. Ed. 2006, 45, 154.
Acknowledgements
The authors are thankful to Dr.Jeyaprakash and Dr. Sathya
Shanker, Syngene Intl. Ltd. for their valuable suggestions and
support during the course of this project.
Key Words: Reductive carbonylation; Cobalt carbonyl; Bimetallic
catalyst; Formylation.
References
[1] a) L. S. Starkey, Ed. Introduction to Strategies for Organic Synthesis; John
Wiley & Sons: Hoboken, NJ, 2012; Chapter 3.9, pp 105−114. (b) B. M.
Trost, Ed. Comprehensive Organic Synthesis; Pergamon: Oxford, 1991;
Vol 8, pp 259−305. (c) J. Pospech, I. Fleischer, R. Franke, S. Buchholz
and M. Beller, Angew. Chem., Int. Ed., 2013, 52, 2852; d) R. Franke, D.
Selent and A. Börner, Chem. Rev., 2012, 112, 5675; e) G. T. Whiteker
and C. J. Cobley, Top. Organomet. Chem., 2012, 42, 35.
[2] a) F. Aldabbagh, Compr. Org. Funct. Group Transform. II, 2005, 3, 9; b) L.
P. Crawford, S. K. Richardson, Gen. Synth. Method, 1994, 16, 37 – 91.
[3] a) A. Brennführer, H. Neumann, M. Beller, Angew. Chem., Int. Ed., 2009, 48,
4114; b) C. F. J. Barnard, Organometallics, 2008, 27, 5402; c) A.
Brennfuhrer, H. Neumann, S. Klaus, T. Riermeier, J. Almena, M. Beller,
Tetrahedron, 2007, 63, 6252; d) C. F. J. Barnard, Org. Process Res. Dev.
2007, 11, 39.
[4] a) A. Schoenberg, R. F. Heck, J. Am. Chem. Soc. 1974, 96, 7761; b) V. P.
Baillargeon, J. K. Stille, J. Am. Chem. Soc. 1983, 105, 7175; c) V. P.
Baillargeon, J. K. Stille, J. Am. Chem. Soc. 1986, 108, 452; c) W. J. Scott,
G. T. Crisp, J. K. Stille, J. Am. Chem. Soc. 1984, 106, 4630; d) A. B.
Smith III, Y. S. Cho, H. Ishiyama, Org. Lett. 2001, 3, 3971; e) I. Pri-Bar,
O. Buchman, J. Org. Chem. 1984, 49, 4009; f) Y. Misumi, Y. Ishii, M.
Hidai, Organometallics. 1995, 14, 1770; g) H. Kotsuki, P. K. Datta, H.
Suenaga, Synthesis. 1996, 470.
[5] a) For a review on carbonylation without CO gas, see: T. Morimoto, Kakiuchi,
Angew. Chem. Int. Ed. 2004, 43, 5580; b) S. Cacchi, G. Fabrizi, A.
Goggiamani, Org. Lett. 2003, 5, 4269; c) G. Lesma, A. Sacchetti, A.
Silvani, Synthesis. 2006, 594.
[6] S. Ko, H. Han, S. Chang, Org. Lett. 2003, 5, 2687.
[7] a) J.-P. Simonato, T. Walter, P. Mtivier, J. Mol. Catal. A. 2001, 171, 91; b) J.-
P. Simonato, J. Mol. Catal. A. 2003, 197, 61.
[8] S. D Friis, T. L. Andersen, T. Skrydstrup, Org. Lett. 2013, 15, 1378.
[9] a) P. Hermange, A. T. Lindhardt, R. H. Taaning, K. Bjerglund, D. Lupp, T.
Skrydstrup, J. Am. Chem. Soc. 2011, 133, 6061; b) P. Hermange, T. M.
Gøgsig, A. T. Lindhardt, R. H. Taaning, T. Skrydstrup, Org. Lett. 2011,
13, 2444; c) Z. Xin, T. M. Gøgsig, A. T. Lindhardt, T. Skrydstrup, Org.
Lett. 2012, 14, 284.
[10] a) For a recent review on Mo(CO)6, see: L. R. Odell, F. Russo, M. Larhed,
Synlett. 2012, 685; b) P. Baburajan, R. Senthilkumaran, K. P. Elango,
New J. Chem. 2013, 37, 3050.
[11] a) S. N. Gockel, K. L. Hull, Org. Lett. 2015, 17, 3236; b) K. Fuji, T. Morimoto,
K. Tsutsumi, K. Kaiuchi, Angew. Chem. Int. Ed. 2003, 42, 2409.
[12] J. T. Joseph, A. M. Sajith, R. C. Ningegowda, S. Shashikanth, Adv. Synth.
Catal. 2017, 359, 419.
[13] S. Korsager, R. H. Taaning, A. T. Lindhardt, T. Skrydstrup, J. Org. Chem.
2013, 78, 6112.
[14] a) T. Ueda, H. Konishi, K. Manabe, Angew. Chem. 2013, 125, 8773; Angew.
Chem. Int. Ed. 2013, 52, 8611; b) T. Ueda, H. Konishi, K. Manabe, Org.
Lett. 2013, 15, 5370.
[15] K. Natte, A. Dumrath, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2014,
53, 10090.
5
This article is protected by copyright. All rights reserved.