Article
Chemistry, Multidisciplinary
Jilei Cao, Xiaona Yang, Lishuang Ma, Kanghui Lu, Rong Zhou
Summary: A synergistic combination of photoredox and polarity reversal catalysis enabled a novel approach for the generation of silyl cation via visible-light photoredox catalysis, facilitating the dehydrogenative cross-coupling of Si-H and O-H in good yields and broad substrate scope. The reaction proceeded smoothly without the need for any metals, external oxidants, or proton reductants, unlike traditional photocatalytic hydrogen evolution cross-coupling reactions.
Article
Chemistry, Organic
Jake J. Blackner, Deirdre M. Rooney, Joshua W. Hollett, J. Adam McCubbin
Summary: A boronic acid catalyzed carbon-carbon and carbon-nitrogen bond-forming reaction using ferrocenium boronic acid hexafluoroantimonate salt as catalyst has been developed for the functionalization of various pi-activated alcohols. The reaction proceeds under mild conditions and yields up to 98%, with higher yields and selectivity observed when using organosilane nucleophiles. Computational studies provide a mechanistic pathway for the retention of E/Z stereochemistry when using alkenyl silanes as nucleophiles. This methodology is effective with a variety of organosilane nucleophile sub-types, including allylic, vinylic, and propargylic trimethylsilanes.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Wei-Guo Xiao, Bin Xuan, Li-Jun Xiao, Qi-Lin Zhou
Summary: Molecules with an allylic amine motif are important for building biologically relevant chemical space. This study presents an efficient catalytic multicomponent coupling reaction, using nickel and Lewis acid catalysis, to synthesize architecturally complex and functionally diverse allylic amines in one step. The method is simple, tolerant to different functional groups, and allows the synthesis of drug-like allylic amines not accessible by other methods. The use of accessible starting materials and inexpensive catalyst provides practical advantages.
Article
Chemistry, Organic
Dandan Sun, Thayalan Rajeshkumar, Yifan Li, Jiaxin Xu, Runkai Chen, Zhaohua Wan, Zongchao Lv, Laurent Maron, Yi-Hung Chen
Summary: Transition-metal-catalyzed cross-coupling of propargylic electrophiles and Grignard reagents provides useful synthetic intermediates. However, few examples exist for the conversion of propargylic derivatives into propargyl compounds due to the challenging regioselectivity. We demonstrate a regioselective and stereospecific propargylation of Grignard reagents using LaCl3.2LiCl as a catalyst in the absence of a ligand.
Article
Chemistry, Organic
Xiao-Wen Wang, Rui-Xue Li, Yang Deng, Ming-Qiu-Hao Fu, Ya-Nan Zhao, Zhi Guan, Yan-Hong He
Summary: This article proposes a new method for the direct hydroxylarylation of unactivated benzylic carbons (sp3/sp2/sp) without the need for pre-functionalized benzylic alcohols, aromatic aldehydes, or ketones. It features direct functionalization of unactivated benzylic C(sp3)-H bonds and benzylic sp2/sp-carbons, mild conditions (open air, room temperature), an environmentally friendly procedure (without any external catalyst/mediator/additive), and direct access to sterically hindered alcohols from inexpensive and readily available alkyl/alkenyl/alkynylbenzenes. Mechanistic studies strongly support the proposed radical-radical cross-coupling between transient ketyl radicals and persistent radical anions. Gram-scale synthesis and diversification of drug derivatives demonstrate the practical potential of this protocol.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xing-Long Zhang, Rui-Li Guo, Meng-Yue Wang, Bao-Yin Zhao, Qiong Jia, Jin-Hui Yang, Yong-Qiang Wang
Summary: The unprecedented palladium-catalyzed three-component dehydrogenative cascade coupling method introduces a C5 structural unit into indoles with high selectivity and a broad substrate scope, making it an economical and efficient approach.
Article
Chemistry, Organic
Ying Lin, Liang Zou, Renren Bai, Xiang-Yang Ye, Tian Xie, Yang Ye
Summary: We present an easy and efficient method for vinylation using Fe-catalyzed cross-electrophile coupling of readily available vinyl- and hydro-chlorosilanes with a range of substituted alkenyl bromides using manganese as the terminal reductant. This modular approach allows the formation of various vinyl orgaonosilanes, including electron-rich, electron-poor, and ortho-/meta-/para-substituted vinyl electrophiles, with excellent functional group tolerance and broad substrate scope. Furthermore, this method successfully modified substrates with structurally complex natural products and pharmaceutical motifs, demonstrating its potential in gram-scale reactions and derivatization.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Hidenori Matsuyama, Xuan Zhang, Masahiro Terada, Tienan Jin
Summary: A versatile method for synthesizing alkylidene fluorenes and their heteroarene derivatives has been successfully developed by using a Pd(II)-catalyzed direct C-H/C-H coupling of o-alkenyl biaryls. Under aerobic oxidation conditions, the use of Pd(OAc)2 catalyst produces alkylidene fluorenes with various functional groups and diverse polycyclic systems. These resulting products can be utilized as versatile synthetic building blocks for constructing structurally diverse polycyclic arenes and heteroarenes.
Article
Chemistry, Organic
Amardeep Ramprasad Jadhao, Sanjay Subhash Gaikwad
Summary: A facile and sustainable copper-catalyzed thiolation method has been developed to efficiently construct benzylic thioethers under mild reaction conditions. This approach avoids the use of commonly employed thiolation reagents, making it an attractive method for benzylic thioether synthesis due to the commercial availability of base and reagents, broad substrate scope, and convenient reaction procedure.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Bo Chen, Xinqi Zheng, Juwen Gu, Songbai Qiu, Jinliang Song, Xiaoping Wu, Huafeng Dong, Qian Zhang, Tiejun Wang
Summary: In this study, the Sn-Ni/CS catalysts were developed to selectively upgrade abundant bio-ethanol to higher alcohols. The synergy between Ni and doped Sn species promoted the enhanced selectivity of higher alcohols, while suppressing the formation of by-products.
APPLIED CATALYSIS B-ENVIRONMENTAL
(2023)
Article
Chemistry, Multidisciplinary
Jiefeng Zhu, Shuyou Chen, Chuan He
Summary: A rhodium-catalyzed enantioselective construction of triorgano-substituted silicon-stereogenic siloxanes and alkoxysilanes has been developed, expanding the chemical space of silicon-centered chiral molecules. The method was further demonstrated by constructing CPL-active silicon-stereogenic alkoxysilane small organic molecules with potential applications in chiral organic optoelectronic materials.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Lanxiao Zhao, Peng Deng, Xun Gong, Xiaohui Kang, Jianhua Cheng
Summary: This study demonstrated the catalytic ortho-regioselective C-H alkylation of alkoxy-substituted benzene derivatives with alkenes using a half-sandwich calcium alkyl complex as the precatalyst. The potential catalytic reaction intermediates were isolated and X-ray structurally characterized, with DFT calculations elucidating the different reaction profiles of sp(2) and sp(3) C-H activations.
Article
Chemistry, Organic
Naveen Yadav, Jabir Khan, Aparna Tyagi, Sanjay Singh, Chinmoy Kumar Hazra
Summary: A regioselective protocol for the synthesis of cyclopropyl derivatives via Brookhart acid-catalyzed dehydrative coupling without rearrangement is reported. The method shows excellent yield, tolerance towards various cyclopropylcarbinols, and an efficient gram-scale reaction with high turnover number.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Sven C. Richter, Martin Oestreich
Summary: The chemoselective deoxygenation of secondary benzylic alcohols can be achieved through a series of formylation and reduction reactions, forming formates. In this process, the formyl group acts as both an activator and a self-sacrificing protecting group, allowing the reaction to proceed in the presence of other reducible groups.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
Mingyang Liu, Paul J. Dyson
Summary: Efficient valorization of lignin, a sustainable and renewable source, is essential for reducing dependence on fossil-derived feedstocks. This study presents a highly efficient strategy for extracting aromatic monomers and generating functionalized diaryl ethers from lignin using oxidative cross-coupling reactions.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Marian Rauser, Daniel P. Warzecha, Meike Niggemann
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Marian Rauser, Christoph Ascheberg, Meike Niggemann
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Applied
Vera J. Meyer, Liang Fu, Fabian Marquardt, Meike Niggemann
ADVANCED SYNTHESIS & CATALYSIS
(2013)
Article
Chemistry, Multidisciplinary
Tobias Haven, Grzegorz Kubik, Stefan Haubenreisser, Meike Niggemann
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2013)
Article
Chemistry, Multidisciplinary
Vera J. Meyer, Meike Niggemann
CHEMISTRY-A EUROPEAN JOURNAL
(2012)
Article
Chemistry, Multidisciplinary
Jeanne-Marie Begouin, Meike Niggemann
CHEMISTRY-A EUROPEAN JOURNAL
(2013)
Article
Chemistry, Organic
Stefan Haubenreisser, Peter Hensenne, Sebastian Schroeder, Meike Niggemann
Article
Chemistry, Organic
Jeanne-Marie Begouin, Francesca Capitta, Xian Wu, Meike Niggemann
Article
Chemistry, Organic
Anastasie Kena Diba, Jeanne-Marie Begouin, Meike Niggemann
TETRAHEDRON LETTERS
(2012)
Editorial Material
Chemistry, Multidisciplinary
Meike Niggemann, Shuang Gao
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Marian Rauser, Raphael Eckert, Max Gerbershagen, Meike Niggemann
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Multidisciplinary
Sebastian Schroeder, Christina Strauch, Niklas Gaelings, Meike Niggemann
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Multidisciplinary
Christina Strauch, Sebastian Schroeder, Gwendal Grelier, Meike Niggemann
Summary: Vinyl triflimides undergo N-Tf bond cleavage through triplet-triplet energy transfer, generating radicals that undergo radical-radical coupling to achieve 1,2-difunctionalization without the need for external CF3 reagents.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Marian Rauser, Christoph Ascheberg, Meike Niggemann
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Meeting Abstract
Chemistry, Multidisciplinary
Tobias Haven, Meike Niggemann
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2012)
