Synthesis and structural characterization of a trispyrrole iron(II) complex K(dme)4[tpaMesFe] and application in nitrous oxide dependent coupling reactions

作者: Maik Weidauer , Elisabeth Irran , Stephan Enthaler

DOI: 10.1016/J.INOCHE.2015.01.028

关键词: Salt (chemistry)MetathesisChemistryBoronic acidCatalysisReagentMannich reactionMedicinal chemistryDeprotonationCoupling reactionOrganic chemistry

摘要: Abstract A new synthetic route to the trispyrrole iron(II) complex {K(dme) 4 [tpa Mes Fe]} was established starting from BOC-protected pyrrol via synthesis of corresponding boronic acid, cross-coupling reaction, deprotection, triple Mannich a deprotonation and finally salt metathesis. The characterized applied in iron-catalyzed coupling reactions. In more detail, with catalytic amounts K(dme) Fe] homo-coupling aromatic Grignard reagents as well hetero-coupling were feasible. Noteworthy, force reaction nitrous oxide added realize yields up 93% at mild conditions.

参考文章(19)
Arvin Mosier, Carolien Kroeze, Cindy Nevison, Oene Oenema, Sybil Seitzinger, Oswald van Cleemput, Closing the global N2O budget: nitrous oxide emissions through the agricultural nitrogen cycle Nutrient Cycling in Agroecosystems. ,vol. 52, pp. 225- 248 ,(1998) , 10.1023/A:1009740530221
A Shimizu, K Tanaka, M Fujimori, Abatement technologies for N2O emissions in the adipic acid industry Chemosphere - Global Change Science. ,vol. 2, pp. 425- 434 ,(2000) , 10.1016/S1465-9972(00)00024-6
Xiang Hong, Mohamed Mellah, Franck Bordier, Régis Guillot, Emmanuelle Schulz, Electrogenerated Polymers as Efficient and Robust Heterogeneous Catalysts for the Hydrolytic Kinetic Resolution of Terminal Epoxides Chemcatchem. ,vol. 4, pp. 1115- 1121 ,(2012) , 10.1002/CCTC.201200085
W. Hill Harman, Christopher J. Chang, N2O activation and oxidation reactivity from a non-heme iron pyrrole platform. Journal of the American Chemical Society. ,vol. 129, pp. 15128- 15129 ,(2007) , 10.1021/JA076842G
Ive Hermans, Bart Moens, Jozef Peeters, Pierre Jacobs, Bert Sels, Diazo chemistry controlling the selectivity of olefin ketonisation by nitrous oxide. Physical Chemistry Chemical Physics. ,vol. 9, pp. 4269- 4274 ,(2007) , 10.1039/B704351A
F. S. Bridson-Jones, G. D. Buckley, L. H. Cross, A. P. Driver, 666. Oxidation of organic compounds by nitrous oxide. Part I Journal of The Chemical Society (resumed). pp. 2999- 3008 ,(1951) , 10.1039/JR9510002999
Dmitry P. Ivanov, Konstantin A. Dubkov, Dmitry E. Babushkin, Sergey V. Semikolenov, Gennady I. Panov, Ketonization of 1,5-Cyclooctadiene by Nitrous Oxide Advanced Synthesis & Catalysis. ,vol. 351, pp. 1905- 1911 ,(2009) , 10.1002/ADSC.200900278
Manabendra Ray, Adina P. Golombek, Michael P. Hendrich, Victor G. Young,, A. S. Borovik, Synthesis and Structure of a Trigonal Monopyramidal Fe(II) Complex and Its Paramagnetic Carbon Monoxide Derivative Journal of the American Chemical Society. ,vol. 118, pp. 6084- 6085 ,(1996) , 10.1021/JA960036K
Manabendra Ray, Brian S. Hammes, Glenn P. A. Yap, Arnold L. Rheingold, A. S. Borovik, Structure and Physical Properties of Trigonal Monopyramidal Iron(II), Cobalt(II), Nickel(II), and Zinc(II) Complexes Inorganic Chemistry. ,vol. 37, pp. 1527- 1532 ,(1998) , 10.1021/IC970831E