N-Heterocyclic carbene/Brønsted acid cooperative catalysis as a powerful tool in organic synthesis

Scholarly Works

• Beng, T. K.; Kaur, J.; Anosike, I. S.; Rentfro, B.; Newgard, S. Revisiting the 1,3-azadiene-succinic anhydride annulation reaction for the stereocontrolled synthesis of allylic 2-oxopyrrolidines bearing up to four contiguous stereocenters. RSC advances 2024, 14, 16678–16684. doi:10.1039/d4ra03156c
• Do, M.; Anosike, S. I.; Beng, T. K. Diastereospecific arylation and cascade deconstructive amidation/thioesterification of readily available lactam-fused bromolactones. RSC advances 2023, 13, 25691–25698. doi:10.1039/d3ra04690g
• Benedetti, E.; Micouin, L. Bicyclic 5-5 Systems With One Bridgehead (Ring Junction) Nitrogen Atom: Two Extra Heteroatoms 2:0. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 145–173. doi:10.1016/b978-0-12-409547-2.14935-2
• Harnying, W.; Sudkaow, P.; Biswas, A.; Berkessel, A. N-Heterocyclic Carbene/Carboxylic Acid Co-Catalysis Enables Oxidative Esterification of Demanding Aldehydes/Enals, at Low Catalyst Loading. Angewandte Chemie (International ed. in English) 2021, 60, 19631–19636. doi:10.1002/anie.202104712
• Harnying, W.; Sudkaow, P.; Biswas, A.; Berkessel, A. N‐Heterocyclic Carbene/Carboxylic Acid Co‐Catalysis Enables Oxidative Esterification of Demanding Aldehydes/Enals, at Low Catalyst Loading. Angewandte Chemie 2021, 133, 19783–19788. doi:10.1002/ange.202104712
• Bhattacharyya, A. Synthetic Routes to 2-Iminothiazolidines: State-of-the-Art 2006-2020. Current Organic Chemistry 2020, 24, 2823–2844. doi:10.2174/1385272824999201019162400
• Hollóczki, O. The mechanism of N‐heterocyclic carbene organocatalysis through a magnifying glass. Chemistry (Weinheim an der Bergstrasse, Germany) 2020, 26, 4885–4894. doi:10.1002/chem.201903021
• Sun, J.; Mou, C.; Wang, Z.; He, F.; Wu, J.; Robin, Y. Carbene-Catalyzed [4 + 2] Cycloadditions of Vinyl Enolate and (in Situ Generated) Imines for Enantioselective Synthesis of Quaternary α-Amino Phosphonates. Organic letters 2018, 20, 5969–5972. doi:10.1021/acs.orglett.8b02707
• Gehrke, S.; Hollóczki, O. Treten in der N-heterozyklischen Carben-Organokatalyse wirklich Carbene auf?. Angewandte Chemie 2017, 129, 16613–16617. doi:10.1002/ange.201708305
• Gehrke, S.; Hollóczki, O. Are There Carbenes in N-Heterocyclic Carbene Organocatalysis?. Angewandte Chemie (International ed. in English) 2017, 56, 16395–16398. doi:10.1002/anie.201708305
• Byers, J. A.; Biernesser, A. B.; Delle Chiaie, K. R.; Kaur, A.; Kehl, J. A. Catalytic Systems for the Production of Poly(lactic acid). Synthesis, Structure and Properties of Poly(lactic acid); Springer International Publishing, 2017; pp 67–118. doi:10.1007/12_2017_20
• Yanlong, L.; Sun, H.; Zhang, W.; Wang, X.; Xu, S.; Zhang, G.; Jian, Y.; Gao, Z. Triple zirconocene/brønsted acid/CuO cooperative and relay catalysis system for tandem Mannich addition/C–C formative cyclization/oxidation. RSC Advances 2017, 7, 28616–28625. doi:10.1039/c7ra00870h
• Li, J.; Lin, L.; Hu, B.; Lian, X.; Wang, G.; Liu, X.; Feng, X. Bimetallic Gold(I)/Chiral N,N′‐Dioxide Nickel(II) Asymmetric Relay Catalysis: Chemo‐ and Enantioselective Synthesis of Spiroketals and Spiroaminals. Angewandte Chemie (International ed. in English) 2016, 55, 6075–6078. doi:10.1002/anie.201601701
• Li, J.; Lin, L.; Hu, B.; Lian, X.; Wang, G.; Liu, X.; Feng, X. Bimetallic Gold(I)/Chiral N,N′‐Dioxide Nickel(II) Asymmetric Relay Catalysis: Chemo‐ and Enantioselective Synthesis of Spiroketals and Spiroaminals. Angewandte Chemie 2016, 128, 6179–6182. doi:10.1002/ange.201601701
• Ghorai, M. K.; Shahi, C. K.; Bhattacharyya, A.; Sayyad, M.; Mal, A.; Wani, I. A.; Chauhan, N. Syntheses of Tetrahydrobenzodiazepines via SN2-Type Ring-Opening of Activated Aziridines with 2-Bromobenzylamine Followed by Copper-Powder-Mediated C−N Bond Formation. Asian Journal of Organic Chemistry 2015, 4, 1103–1111. doi:10.1002/ajoc.201500224
• Jindal, G.; Kisan, H. K.; Sunoj, R. B. Mechanistic Insights on Cooperative Catalysis through Computational Quantum Chemical Methods. ACS Catalysis 2014, 5, 480–503. doi:10.1021/cs501688y
• Zhao, Y.; Wang, Z.-T.; Cheng, Y. N‐Heterocyclic Carbene/Brønsted Base Cascade Catalysis: Base‐Controlled Selective Synthesis of Multifunctional Benzofuran‐3‐ones or Flavone Derivatives from the Reaction of 3‐(2‐Formylphenoxy)propenoates with Imines. Advanced Synthesis & Catalysis 2014, 356, 2580–2590. doi:10.1002/adsc.201400331
• Ghorai, M. K.; Sahoo, A. K.; Bhattacharyya, A. Syntheses of Imidazo-, Oxa-, and Thiazepine Ring Systems via Ring-Opening of Aziridines/Cu-Catalyzed C–N/C–C Bond Formation. The Journal of organic chemistry 2014, 79, 6468–6479. doi:10.1021/jo500888j
• Ostrovskii, V. A.; Trifonov, R. E. Fluorinated Triazoles and Tetrazoles. Fluorine in Heterocyclic Chemistry Volume 1; Springer International Publishing, 2014; pp 459–513. doi:10.1007/978-3-319-04346-3_11
• Sinu, C. R.; Suresh, E.; Nair, V. N-Heterocyclic carbene catalyzed reaction of cinnamils leading to the formation of 2,3,8-triaryl vinyl fulvenes: an uncommon transformation. Organic letters 2013, 15, 6230–6233. doi:10.1021/ol4030748

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