Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents
by
Elwira Bisz 1,*
and Michal Szostak 1,2,*
Elwira Bisz 1,* and Michal Szostak 1,2,*
1
Department of Chemistry, Opole University, 48 Oleska Street, 45-052 Opole, Poland
2
Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102, USA
*
Authors to whom correspondence should be addressed.
Academic Editor: Hans-Joachim Knölker
Molecules 2020, 25(1), 230; https://doi.org/10.3390/molecules25010230
Received: 13 December 2019 / Revised: 31 December 2019 / Accepted: 31 December 2019 / Published: 6 January 2020
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
Aryl benzoates are compounds of high importance in organic synthesis. Herein, we report the iron-catalyzed C(sp2)–C(sp3) Kumada cross-coupling of aryl chlorobenzoates with alkyl Grignard reagents. The method is characterized by the use of environmentally benign and sustainable iron salts for cross-coupling in the catalytic system, employing benign urea ligands in the place of reprotoxic NMP (NMP = N-methyl-2-pyrrolidone). It is notable that high selectivity for the cross-coupling is achieved in the presence of hydrolytically-labile and prone to nucleophilic addition phenolic ester C(acyl)–O bonds. The reaction provides access to alkyl-functionalized aryl benzoates. The examination of various O-coordinating ligands demonstrates the high activity of urea ligands in promoting the cross-coupling versus nucleophilic addition to the ester C(acyl)–O bond. The method showcases the functional group tolerance of iron-catalyzed Kumada cross-couplings.
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Keywords:
iron; cross-coupling; aryl esters; C–O activation; Fe-catalysis; Kumada cross-coupling
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MDPI and ACS Style
Bisz, E.; Szostak, M. Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents. Molecules 2020, 25, 230.
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