Article
Chemistry, Multidisciplinary
Lenka Pallova, Laura Abella, Marion Jean, Nicolas Vanthuyne, Cecile Barthes, Laure Vendier, Jochen Autschbach, Jeanne Crassous, Stephanie Bastin, Vincent Cesar
Summary: The first efficient chiral helicene-NHC gold(I) complexes for enantioselective catalysis have been synthesized. Their structural and stereochemical characterization confirms their potential in asymmetric catalysis, demonstrated by the benchmark cycloisomerization reaction with high enantiomeric excess.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Yuan-Yuan Xu, Zhong-Hua Gao, Cao-Bo Li, Song Ye
Summary: The enantioselective alpha-oxidative coupling of enals with carboxylic acids was achieved by umpolung of an NHC-bound enolate with an iodine(III) reagent. The reaction produced alpha-acyloxyl-beta,gamma-unsaturated esters in good yields, with high regio- and enantioselectivities. The reaction involved the formation of an enol iodine(III) intermediate from the enolate with iodosobenzene, which changed the polarity of the enal's alpha-carbon from nucleophilic to electrophilic and facilitated the subsequent carboxylate addition.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Bastiaan Kooij, Zhaowen Dong, Paul Varava, Farzaneh Fadaei-Tirani, Rosario Scopelliti, Laura Piveteau, Kay Severin
Summary: This study reports the preparation and structural characterization of vanadium complexes with N-heterocyclic vinylidene ligands, enabled by utilizing diazoolefins as ligand precursors. Structural and theoretical analysis show that N-heterocyclic vinylidenes can act as strong 6e(-) donor ligands, forming strong metal-carbon interactions.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Hyunho Kim, Minseop Kim, Hayoung Song, Eunsung Lee
Summary: The synthesis of ambiphilic N-heterocyclic carbene ligand indol-2-ylidene (IdY, A) was described, along with its ambiphilicity and synthetic utility. Experimental and computational studies showed that IdY lies between CAAC-5 and CAArC, with copper complexes capable of carboboration of terminal alkynes with high regioselectivity and good yields within 30 minutes.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Wacharee Harnying, Panyapon Sudkaow, Animesh Biswas, Albrecht Berkessel
Summary: Simple carboxylic acids, like benzoic acid, have been found to enhance the activity of N-heterocyclic carbene (NHC) catalysts in the oxidative esterification of aldehydes. A protocol using a novel N-Mes-/N-2,4,6-trichlorophenyl 1,2,4-triazolium salt as catalyst and benzoic acid as co-catalyst was developed for the transformation of a wide range of sterically hindered alpha- and beta-substituted aliphatic aldehydes/enals. The observed effect is believed to be due to the carboxylic acid-induced acceleration of acyl transfer from azolium enolate intermediates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Wu Yuzhu, Shen Panpan, Duan Wenzeng, Ma Yudao
Summary: The first carbene-catalyzed enantioselective 1,6-conjugate addition of boron to para-quinone methides was achieved using a commercially available chiral triazolium and bis(pinacolato)diboron. This reaction features mild conditions, broad substrate scope, excellent functional group tolerance, and good yield and enantioselectivity. Remarkably, even in the absence of any transition metals, the reaction proceeded well with just 0.1 mol% of catalyst loading without significant loss of yield and enantioselectivity, although longer reaction time was required.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Soumen Barik, Sayan Shee, Soumik Das, Rajesh G. Gonnade, Garima Jindal, Subrata Mukherjee, Akkattu T. Biju
Summary: This study describes the atroposelective synthesis of N-aryl succinimides with axially chiral C-N bonds catalyzed by N-heterocyclic carbenes, achieving good yields and ee values. Preliminary investigations were also conducted on the rotation barrier for the C-N bond, temperature dependence, and detailed DFT studies on the mechanism.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Zeyu Han, Derek P. Gates
Summary: This study discovered a high-yielding P=C bond metathesis of phosphaalkenes catalyzed by N-heterocyclic carbenes, resulting in cyclic oligomers formally derived from ArP=PAr. Preliminary mechanistic studies revealed NHC=PAr as key phosphinidene transfer agents, and novel cyclic intermediates were observed. This work represents a rare application of non-metal-based catalysts for transformations involving main-group elements.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Inorganic & Nuclear
Sofie M. P. Vanden Broeck, Catherine S. J. Cazin
Summary: This review focuses on manganese complexes bearing N-heterocyclic carbene (NHC) ligands. The complexes exhibit different properties in various oxidation states and are widely used in catalytic reactions, particularly in CO2 reduction, hydrosilylation and alkylation.
Article
Chemistry, Organic
Hsien-Liang Cho, Chien-Chen Lai, Yi-Hung Liu, Hsiu-Fu Hsu, Shie-Ming Peng, Sheng-Hsien Chiu
Summary: This paper reports the insertion of Pd(II) into an initially achiral rotaxane, resulting in two chiral metallorotaxanes. Chiral additives and chiral TRISPHAT counteranions were used to confirm the existence of chirality and resolve the enantiomers of the C-2-symmetrical N-heterocyclic carbene complex.
Review
Chemistry, Multidisciplinary
G. Mahantesh, Deepika Sharma, Rambabu Dandela, Vasudevan Dhayalan
Summary: This article reviews the synthesis and properties of N-heterocyclic olefins (NHO), as well as their applications as catalysts in organic synthesis. NHOs display electron-rich and polar characteristics, as well as strong basicity, making them highly promising catalysts with great chemical potential.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Benon P. Maliszewski, Tahani A. C. A. Bayrakdar, Perrine Lambert, Lama Hamdouna, Xavier Trivelli, Luigi Cavallo, Albert Poater, Marek Belis, Olivier Lafon, Kristof Van Hecke, Dominic Ormerod, Catherine S. J. Cazin, Fady Nahra, Steven P. Nolan
Summary: In this study, the catalytic activity of a series of platinum(II) pre-catalysts with N-heterocyclic carbene (NHC) ligands in the alkene hydrosilylation reaction is reported. The structural and electronic properties of these catalysts are fully characterized using X-ray diffraction analysis and nuclear magnetic resonance spectroscopy (NMR). A structure-activity relationship within this group of pre-catalysts is established, and mechanistic insights into the catalyst activation step are provided. One of the complexes shows exceptional catalytic performance, achieving a turnover number (TON) of 970,000 and a turnover frequency (TOF) of 40,417 h(-1) at 1 ppm catalyst loading. Furthermore, a solvent-free and open-to-air alkene hydrosilylation protocol with efficient platinum removal (reducing residual Pt from 582 ppm to 5.8 ppm) is disclosed.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Inorganic & Nuclear
Pengcheng Gao, Michal Szostak
Summary: The catalytic addition of water to unsaturated C-C or C-N p bonds is an important and environmentally sustainable method for forming C-O bonds. Traditional acid-catalyzed hydration requires strong acids or toxic mercury salts, limiting its practical applications and posing safety and environmental concerns. Transition-metal-catalyzed hydration with NHC ligands has gained significant attention and has achieved major progress. This review provides a comprehensive overview of hydration reactions catalyzed by transition metal-NHC complexes and their applications in catalytic hydration.
COORDINATION CHEMISTRY REVIEWS
(2023)
Review
Chemistry, Multidisciplinary
Changpeng Chen, Feng-Shou Liu, Michal Szostak
Summary: The discovery of NHCs as ancillary ligands has greatly improved catalytic processes, with BIAN-NHC ligands in particular showing enhanced reactivity due to combinations of electronic and steric properties. The development of BIAN-NHC ligands has led to major advancements in catalysis and offers a practical alternative to classical NHCs.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Cesar Ruiz-Zambrana, Ana Gutierrez-Blanco, Sergio Gonell, Macarena Poyatos, Eduardo Peris
Summary: Two NDI-functionalized complexes of rhodium and iridium were prepared using NDI bis-imidazolium salts as N-heterocyclic carbene precursors. Reduction of the complexes resulted in enhanced electron-richness of the metal and increased catalytic activity in cycloisomerization reactions of alkynoic acids. Two-electron reduction of the ligand further enhanced the catalytic activity, demonstrating the catalyst's ability to switch between three redox species with distinct catalytic activities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Zhong-Lin Zang, Sheng Zhao, Shuklachary Karnakanti, Cheng-Lin Liu, Pan-Lin Shao, Yun He
Article
Chemistry, Organic
Pan-Lin Shao, Zi-Rui Li, Zhi-Peng Wang, Ming-Hui Zhou, Qi Wu, Ping Hu, Yun He
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Zhi-Peng Wang, Zi-Rui Li, Qi Wu, Xiao-Jiao Peng, Pan-Lin Shao, Yun He
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Materials Science, Multidisciplinary
Qiang Zheng, Ping Hu, Qing Tang, Meiqiong Tang, Zhonglin Zang, Sheng Zhao, Panlin Shao, Zhen Wang, Yun He
Article
Chemistry, Organic
Zhen Wang, Huacheng Xu, Qin Su, Ping Hu, Pan-Lin Shao, Yun He, Yixin Lu
Article
Chemistry, Organic
Zhong-Lin Zang, Shuklachary Karnakanti, Sheng Zhao, Ping Hu, Zhen Wang, Pan-Lin Shao, Yun He
Article
Chemistry, Organic
Xiao-Jiao Peng, Yee Ann Ho, Zhi-Peng Wang, Pan-Lin Shao, Yu Zhao, Yun He
ORGANIC CHEMISTRY FRONTIERS
(2017)
Article
Chemistry, Multidisciplinary
Germaine Pui Yann Kok, Pan-Lin Shao, Jia-Yu Liao, Siti Nur Fairuz Bte Sheikh Ismail, Weijun Yao, Yixin Lu, Yu Zhao
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Organic
Zhi-Peng Wang, Sichuan Xiang, Pan-Lin Shao, Yun He
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Zhi-Peng Wang, Yun He, Pan-Lin Shao
ORGANIC & BIOMOLECULAR CHEMISTRY
(2018)
Article
Chemistry, Organic
Zhi-Peng Wang, Qi Wu, Jia Jiang, Zi-Rui Li, Xiao-Jiao Peng, Pan-Lin Shao, Yun He
ORGANIC CHEMISTRY FRONTIERS
(2018)
Article
Chemistry, Multidisciplinary
Yahui Niu, Rong Wang, Panlin Shao, Yuxiu Wang, Yanrong Zhang
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Multidisciplinary
Guangda Xu, Guoqiang Yang, Yue Wang, Pan-Lin Shao, Jia Ning Nicolette Yau, Bing Liu, Yunbo Zhao, Ye Sun, Xinxin Xie, Shuo Wang, Yao Zhang, Lixin Xia, Yu Zhao
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Multidisciplinary
Qi Wu, Pan-Lin Shao, Yun He
Article
Chemistry, Multidisciplinary
Shuklachary Karnakanti, Zhong-Lin Zang, Sheng Zhao, Pan-Lin Shao, Ping Hu, Yun He
CHEMICAL COMMUNICATIONS
(2017)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
