Article
Chemistry, Physical
Laura Talavera, Robert R. A. Freund, Huihui Zhang, Matthew Wakeling, Mara Jensen, Ruben Martin
Summary: In this study, a novel Ni-catalyzed 1,1-difunctionalization reaction of unactivated terminal alkenes is disclosed, allowing for the incorporation of two different heteroatom motifs across an olefin backbone. This method provides a streamlined approach to the synthesis of alpha-aminoboronic acid derivatives from simple precursors and exhibits simplicity and generality across a wide range of coupling counterparts.
Article
Chemistry, Physical
Laura Talavera, Robert R. A. Freund, Huihui Zhang, Matthew Wakeling, Mara Jensen, Ruben Martin
Summary: Here, a novel Ni-catalyzed 1,1-difunctionalization of unactivated terminal alkenes is disclosed, allowing for the incorporation of two different heteroatom motifs across an olefin backbone. This streamlines the access to alpha-aminoboronic acid derivatives from simple precursors, and the method exhibits simplicity and generality across a wide range of coupling counterparts.
Article
Chemistry, Multidisciplinary
Zeqin Yuan, Simin Wang, Miaomiao Li, Tian Chen, Jiaye Fan, Fuying Xiong, Qianggen Li, Ping Hu, Bi-Qin Wang, Peng Cao, Yang Li
Summary: An air and water insensitive visible light induced hydrophosphinylation of unactivated alkenes is carried out using a small amount of salicylaldehyde as a photosensitizer in a basic aqueous solution.
Article
Chemistry, Multidisciplinary
Zhan Dong, Qiongyao Tang, Changyu Xu, Li Chen, Haiting Ji, Sitian Zhou, Liangliang Song, Liang-An Chen
Summary: Transition-metal catalyzed intermolecular 1,2-diarylation of electronically unactivated alkenes is a widely studied topic, but most examples are limited to terminal alkenes. Furthermore, the asymmetric 1,2-diarylation of unactivated alkenes remains unsolved and is challenging. In this study, a highly efficient directed nickel-catalyzed reductive 1,2-diarylation of unactivated internal alkenes with high diastereoselectivities is described. Moreover, enantioselective 1,2-diarylation of unactivated terminal and challenging internal alkenes is achieved with good to high enantioselectivities and high diastereoselectivities by generating a cationic Ni-catalyst through the addition of alkali metal fluoride.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Yiting Hao, Xinlin Wang, Yumeng Wu, Liangliang Song, Kui Zhang, Lingchao Cai
Summary: A concise and modular method for the synthesis of chiral organic compounds bearing pyridyl-substituted stereogenic centers has been established. The method enables the introduction of stereogenic C-(sp(3)) centers into widely available alkenes via a nickel/Box catalyst with alpha-pyridyl alkyl bromide. The reaction conditions are mild and allow for a wide substrate scope and good functional-group tolerance, resulting in the formation of various enantioenriched alkylated pyridine derivatives with high yields and enantioselectivities. Further application of enantioenriched pyridine derivatives is demonstrated through an asymmetric Si-H bond insertion reaction, showcasing the productive utility of this modular strategy.
Article
Chemistry, Multidisciplinary
Chuanqi Hou, Pinhong Chen, Guosheng Liu
Summary: This study reports a palladium-catalyzed Markovnikov hydroalkynylation reaction for the synthesis of branched alkynyl compounds. The reaction shows excellent functional group tolerance, high reaction yields, and good regioselectivity. Moreover, asymmetric hydroalkynylation has been achieved by introducing a chiral ligand.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Physical
Vivek Aryal, Lucas J. Chesley, Doleshwar Niroula, Rishi R. Sapkota, Roshan K. Dhungana, Ramesh Giri
Summary: We have disclosed a novel Ni-catalyzed alkylarylation reaction of electron-deficient alkenes, which allows the construction of two carbon-carbon bonds. The electron-deficient alkenes play a crucial role in stabilizing reaction intermediates and enhancing the catalytic rates. This reaction is also applicable to secondary alkylzinc reagents and internal alkenes, and exhibits excellent regio- and stereocontrol, leading to products with up to three contiguous all-carbon all-cis secondary stereocenters.
Article
Chemistry, Multidisciplinary
Shan-Xiu Ni, Yan-Lin Li, Hui-Qi Ni, Yu-Xiang Bi, Jie Sheng, Xi-Sheng Wang
Summary: A nickel-catalyzed direct hydromonofluoromethylation of unactivated olefins with fluoroiodomethane is developed, providing various primary alkyl fluorides in an efficient and environmentally friendly manner. This transformation shows good functional-group compatibility and holds great potential in drug discovery.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Physical
Peng-Fei Yang, Jian-Xing Liang, Han -Tong Zhao, Wei Shu
Summary: In this study, a straightforward method to access enantioenriched 1,n-diamines containing a chiral alpha-branched aliphatic amine is achieved through Ni-catalyzed asymmetric hydroamination. This method delivers good yields and excellent enantioselectivities with diverse substitution patterns, and exhibits excellent functional group tolerance.
Article
Chemistry, Organic
Sen Yang, Hao Hu, Ming Chen
Summary: A highly efficient visible-light-induced elimination method for alkyl halides is presented, which selectively yields unactivated terminal olefins vital in organic synthesis.
Article
Chemistry, Organic
Sen Yang, Hao Hu, Ming Chen
Summary: A highly efficient method for visible-light-induced regio- and chemoselective elimination of alkyl halides yielding unactivated terminal olefins vital in organic synthesis is presented. The reaction, achieved through ligand control, exhibits remarkable regioselectivity and suppresses undesired side reactions, particularly 1,5-hydrogen atom transfer (HAT). This method favors primary alkyl halides while preserving secondary and tertiary alkyl bromides, thereby enabling the incorporation of terminal olefins in complex molecules for late-stage functionalization.
Article
Chemistry, Multidisciplinary
Tao Zhong, Ji-Tao Yi, Zhi-Da Chen, Quan-Can Zhuang, Yong-Zhao Li, Gui Lu, Jiang Weng
Summary: This study successfully reported the first three-component aminofluorosulfonylation of unactivated olefins by merging photoredox-catalyzed proton-coupled electron transfer (PCET) activation with radical relay processes, efficiently affording various aliphatic sulfonyl fluorides featuring a privileged 5-membered heterocyclic core under mild conditions with good functional group tolerance. The synthetic potential of the sulfonyl fluoride products was examined by diverse transformations including SuFEx reactions and transition metal-catalyzed cross-coupling reactions, with mechanistic studies demonstrating the involvement of amidyl radicals, alkyl radicals, and sulfonyl radicals in this difunctionalization transformation.
Article
Chemistry, Multidisciplinary
Benxiang Zhang, Jiayan He, Yi Li, Tao Song, Yewen Fang, Chaozhong Li
Summary: Acylphosphonates with the 5,5-dimethyl-1,3,2-dioxophosphinanyl skeleton have been developed as efficient intermolecular radical acylation reagents for cobalt-catalyzed Markovnikov hydroacylation of unactivated alkenes at room temperature. The protocol shows broad substrate scope and good functional group compatibility, providing satisfactory yields of branched ketones. The proposed mechanism involves Co-H mediated hydrogen atom transfer and subsequent trapping of alkyl radicals by acylphosphonates.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Multidisciplinary Sciences
Geun Seok Lee, Daeun Kim, Soon Hyeok Hong
Summary: The use of alkyl chlorides in Pd-catalyzed Mizoroki-Heck coupling reactions remains a challenging issue due to the high thermodynamic barrier of alkyl chloride activation and the propensity of alkylpalladium complexes to undergo undesired beta-hydride elimination. However, this study demonstrates that alkyl chlorides, including tertiary ones, can efficiently participate in Mizoroki-Heck cross-coupling reactions under mild conditions via photoinduced Pd catalysis, offering great potential for late-stage functionalizations and molecular complexity.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Yang Yuan, Youcan Zhang, Wenbo Li, Yanying Zhao, Xiao-Feng Wu
Summary: A novel method for constructing amide bonds through anti-Markovnikov hydroaminocarbonylation of unactivated alkenes has been developed. Copper catalysis, hydroxylamine electrophile reagents, and poly(methylhydrosiloxane) (PMHS) were used under mild conditions. The reaction showed a high degree of tolerance towards various functional groups and efficiently converted unactivated terminal alkenes, 1,1-disubstituted alkenes, and cyclic alkenes to the corresponding amides with exclusive anti-Markovnikov selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Benjamin G. Janesko, Henry C. Fisher, Mark J. Bridle, Jean-Luc Montchamp
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
Vincent Richard, Henry C. Fisher, Jean-Luc Montchamp
TETRAHEDRON LETTERS
(2015)
Review
Chemistry, Multidisciplinary
Theresa Sperger, Henry C. Fisher, Franziska Schoenebeck
WILEY INTERDISCIPLINARY REVIEWS-COMPUTATIONAL MOLECULAR SCIENCE
(2016)
Article
Biochemical Research Methods
Paul W. A. Devine, Henry C. Fisher, Antonio N. Calabrese, Fiona Whelan, Daniel R. Higazi, Jennifer R. Potts, David C. Lowe, Sheena E. Radford, Alison E. Ashcroft
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
(2017)
Article
Chemistry, Applied
Henry C. Fisher, Olivier Berger, Fabien Gelat, Jean-Luc Montchamp
ADVANCED SYNTHESIS & CATALYSIS
(2014)
Article
Chemistry, Organic
Henry C. Fisher, Lucie Prost, Jean-Luc Montchamp
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2013)
Article
Virology
Judit Voeroes, Annika Urbanek, Gilles Jean Philippe Rautureau, Maggie O'Connor, Henry C. Fisher, Alison E. Ashcroft, Neil Ferguson
JOURNAL OF VIROLOGY
(2014)
Article
Biochemical Research Methods
Henry C. Fisher, Marco Smith, Alison E. Ashcroft
RAPID COMMUNICATIONS IN MASS SPECTROMETRY
(2013)
Article
Chemistry, Multidisciplinary
Alexander B. Duerr, Henry C. Fisher, Indrek Kalvet, Khai-Nghi Truong, Franziska Schoenebeck
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Meeting Abstract
Chemistry, Multidisciplinary
Henry C. Fisher, Mark Bridle, Benjamin G. Janesko, Jean-Luc Montchamp
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2014)
Article
Chemistry, Organic
Charles M. Garner, Henry C. Fisher
TETRAHEDRON LETTERS
(2006)