Abstract
The industrial process of hydroformylation or the oxo process has been used for many years in the production of aldehydes from alkenes. Different metals have been used as efficient catalysts for hydroformylation, in which linear and branched aldehydes are the products obtained; therefore, the development of new catalysts for hydroformylation with high selectivity to aldehydes is important. Rhodium complexes 6–9 were synthesized using [RhCl(CO)2]2, or [RhCl(COD)]2, with either pyrazolylpyridyl N′N′N pincer ligands or a pyrazolylpyridyl N′N ligand. These complexes were then evaluated as catalyst precursors in the hydroformylation reaction using a variety of alkenes. The catalysts all showed activity in hydroformylation but the most active catalyst was methyl-substituted pyrazolyl–rhodium complex 7 following optimization of temperature, syngas pressure and amount of catalyst. Other olefinic substrates were used for hydroformylation in the presence of 7 under the optimum hydroformylation conditions. Undecene and dodecene as substrates only showed minimal formation of aldehydes with predominantly isomerization of the alkene being observed.
Similar content being viewed by others
References
Maximilian A, Hertrich F, Scharnagl FK, Pews-Davtyan A, Kreyenschulte C, Lund H, Bartling S, Jackstell R, Beller M (2019) Chem A Eur J. https://doi.org/10.1002/chem.201806282
Jan JMB, Oliver T, Paciello R, Thomas S, Hofmann P (2016) ACS Catal 6:2802–2810
Tan R, Zheng X, Qu B, Sader CA, Fandrick KR, Senanayake CH, Zhang X (2016) Org Lett 18:10–13
Wang X (2015) J Flow Chem 5:125–132
Whiteker GT, Cobley CJ (2012) Top Organomet Chem 42:35–46
Pospech J, Fleischer I, Franke R, Buchholz S, Beller M (2013) Angew Rev 52:2852–2872
Le L, Couturier J, Dubois J (2016) J Mol Catal A 417:116–121
Sun Q, Dai Z, Liu X, Sheng N, Deng F, Meng X, Xiao F, Sun Q, Dai Z, Liu X, Sheng N, Deng F, Meng X (2015) J Am Chem Soc. https://doi.org/10.1021/jacs.5b02122
Brezny AC, Landis CR (2018) Acc Chem Res 51:2344–2354
Matsui Y, Orchin M (1983) J Organomet Chem 246:57
Naim M, Alam O, Nawaz F, Alam MJ, Alam P (2015) J Pharm Bioallied Sci 8:2–17
Lamsayah M, Khoutoul M, Takfaoui A, Abrigach F, Oussaid A, Touzani R (2015) Sep Sci Technol 50:2170–2176
Ruman T, Lukasiewicz M, Ciunik Z, Wolowiec S (2001) Polyhedron 20:2551–2558
Teuma E, Loy M, Le Berre C, Etienne M, Daran J, Kalck P (2003) Organometallics 22:5261–5267
Oro LA, Pinillos T, Uson R (1982) J Mol Catal 14:375–378
Lyubimov SE, Rastorguev EA, Davankov VA (2012) Russ Chem Bull 61:2356–2359
Ren X, Zheng Z, Zhang L, Wang Z, Xia C, Ding K (2016) Angew Chem Int Ed Engl 55:1–5
Touzani R (2014) Arab J Chem Environ Res 1:76–99
Gramage-doria R, Raoufmoghaddam S, Parella T (2015) J Am Chem Soc 137:2680–2687
Segapelo TV, Guzei IA, Spencer LC, Van Zyl WE, Darkwa J (2009) Inorg Chim Acta 362:3314–3324
Kapfunde T (2018) University of Johannesburg
RajanBabu TV, Ayers TA (1994) Tetrahedron Lett 35:4295–4298
Acknowledgements
We acknowledge the National Research Foundation of South Africa (NRF) (Grant Nos. 105557, 117989), The Technology and Human Resource for Industry Programme (THRIP), (Grant No. THRIP/58/30/11/2017), Sasol SA Ltd (University Collaboration Programme) and the University of Johannesburg’s Centre for Synthesis and Catalysis for financial support.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
All authors declare that they have no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Gamede, N.V., Kapfunde, T.A., Ocansey, E. et al. N′N′N pincer and N′N bidentate(pyrazolylpyridyl) Rh(I) complexes as catalyst precursors for hydroformylation of olefins. Transit Met Chem 45, 1–8 (2020). https://doi.org/10.1007/s11243-019-00350-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11243-019-00350-2