Article
Chemistry, Organic
Mingdong Jiao, Xianjie Fang
Summary: A novel synthesis of homoallylic nitriles via cobalt-catalyzed hydrocyanation of methylenecyclopropanes is described. The protocol demonstrates excellent selectivity, mild reaction conditions, good functional group compatibility, gram-scale reaction, and product transformations. The extraordinary selectivity is probably attributed to the stronger aptitude of the alkyl-cobalt cyanide intermediate for reductive elimination rather than beta-hydride elimination.
Article
Chemistry, Multidisciplinary
Philip Boehm, Niklas Kehl, Bill Morandi
Summary: A rhodium-catalyzed anti-Markovnikov hydroiodination reaction was performed on both aromatic and aliphatic terminal alkynes, resulting in high isomeric purity of (E)- or (Z)-configured alkenyl iodides depending on the ligand and substrate used. The broad substrate scope and high functional group tolerance make this reaction highly versatile. The synthesized vinyl iodides were used successfully in various bond-forming reactions, and the method showed potential for shortening the total synthesis of a marine cis-fatty acid. Initial deuterium-labeling experiments and stoichiometric reactions provided insights into the reaction mechanism.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Ying Ding, Jinguo Long, Xianjie Fang
Summary: A nickel-catalyzed hydrocyanation of aliphatic allenes with excellent regioselectivity has been developed. This protocol features mild reaction conditions and good functional group tolerance, providing an efficient catalytic pathway to access various allylic nitriles containing quaternary carbon centers in a one-step fashion. Additionally, preliminary attempts were made to investigate an asymmetric version of this reaction.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Jihui Gao, Jie Ni, Rongrong Yu, Gui-Juan Cheng, Xianjie Fang
Summary: This highly regioselective nickel-based catalyst system enables the isomerization/hydrocyanation of aliphatic internal olefins, providing a variety of aliphatic nitriles with excellent regioselectivities and good yields under mild conditions. The reaction protocol, under Lewis acid-free conditions, shows broad functional group tolerance, including secondary amine and unprotected alcohol groups.
Article
Chemistry, Applied
Jin Zhang, Cui-Ping Luo, Luo Yang
Summary: A Ni/Co co-catalyzed reductive hydrocyanation of alkynes was developed for the production of saturated nitriles. Formamide played multiple roles as a cyano source, dehydrant, and reductant, supporting various mechanistic pathways.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Multidisciplinary Sciences
Shaowei Chen, Xiaoqian He, Yi Jin, Yu Lan, Xiao Shen
Summary: This study presents a copper-catalyzed selective hydrosilylation reaction method for efficient preparation of (E)-allylsilanes, which shows broad substrate scope and can be used for the synthesis of multisubstituted (E)-allylsilanes.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Hannah S. Slocumb, Shaozhen Nie, Vy M. Dong, Xiao-Hui Yang
Summary: This study demonstrates the first enantioselective hydroselenation of styrenes, accessing organoselenium building blocks with selectivity for the branched isomer. Through a Rh-hydride pathway, C-Se bonds can be formed with excellent regio- and enantiocontrol.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Wenke Dong, Xin Xu, Honghui Ma, Yaqin Lei, Zhenyang Lin, Wanxiang Zhao
Summary: Researchers reported a catalytic enantioselective hydroboration of silyl enol ethers (SEEs) using two new chiral phosphine ligands, featuring mild reaction conditions and a broad substrate scope.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Yoshihiko Morimoto, Takuya Kochi, Fumitoshi Kakiuchi
Summary: The anti-Markovnikov addition of anilines to aliphatic terminal alkynes was achieved using an 8-quinolinolato rhodium/phosphine catalyst system, with the formation of aldimine products facilitated by the use of a strong organic base, 1,1,3,3,-tetramethylguanidine. Substrates with various functional groups, including polar groups like phenolic hydroxy group, are suitable for hydroamination.
HELVETICA CHIMICA ACTA
(2021)
Article
Multidisciplinary Sciences
Jieping Chen, Jiale Ying, Zhan Lu
Summary: In this study, a cobalt-catalyzed selective hydroallylation reaction was developed to synthesize branched 1,4-dienes. The reaction exhibited excellent functional group tolerance and substrate scope, allowing for gram-scale reactions. The proposed mechanism was based on deuterium labeling experiment and kinetic studies.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Feng Wang, Yuecong Guo, Yutong Zhang, Pingping Tang
Summary: The silver-catalyzed dibromotrifluoromethoxylation of terminal alkynes reported provides 1,1-dibromo-2-(trifluoromethoxy)alkenes in good yields and high regioselectivity under mild reaction conditions. The reaction has a broad substrate scope and can be used for late-stage trifluoromethoxylation of complex small molecules. The products can be further modified, offering a convenient method for synthesizing compounds containing the OCF3 group.
Article
Chemistry, Physical
Qiang Huang, Yu-Xuan Su, Wei Sun, Meng-Yang Hu, Wei-Na Wang, Shou-Fei Zhu
Summary: In this study, an operationally simple and mild iron-catalyzed alkylzincation method for terminal alkynes was developed, which can efficiently produce diverse alkenylzinc compounds with high selectivity. The method demonstrates a high anti-Markovnikov selectivity and high cis stereoselectivity, making it a competitive alternative for the selective synthesis of trisubstituted olefins.
Article
Chemistry, Multidisciplinary
Bing Li, Min Liu, Sajid Ur Rehman, Changkun Li
Summary: In this study, we report a Rh-catalyzed highly regio- and enantioselective synthesis of allylic phosphine oxides. By using a specific chiral ligand and in the presence of diphenyl phosphoric acid, carbon-phosphorus bond formation can be achieved.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Physical
Chang-Sheng Wang, Yongqi Yu, Yusuke Sunada, Chen Wang, Naohiko Yoshikai
Summary: This article reports a cobalt-catalyzed carbo- and hydrocyanation reaction of alkynes, which involves C-CN bond cleavage of organic cyanides. A low-valent cobalt-diphosphine catalyst, generated by reduction with Zn, is used to promote the arylcyanation of alkynes with trans-selectivity. Additionally, the addition of Zn(OTf)2 to the catalytic system accelerates the reaction and switches the stereoselectivity.
Article
Chemistry, Multidisciplinary
Yasuyuki Ura
Summary: This paper describes the challenging realization of anti-Markovnikov selectivity in Pd-catalyzed reactions, with key factors including the steric bulkiness of oxygen nucleophiles and electron-deficient cyclic alkenes as additives.
Review
Chemistry, Multidisciplinary
Rui Guo, Junting Chen
Article
Chemistry, Multidisciplinary
Xiang Sun, Junting Chen, Tobias Ritter
Article
Chemistry, Multidisciplinary
Junting Chen, Jiakun Li, Matthew B. Plutschack, Florian Berger, Tobias Ritter
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Jiakun Li, Junting Chen, Ruocheng Sang, Won-Seok Ham, Matthew B. Plutschack, Florian Berger, Sonia Chabbra, Alexander Schnegg, Christophe Genicot, Tobias Ritter
Article
Chemistry, Multidisciplinary
Qiang Cheng, Junting Chen, Songyun Lin, Tobias Ritter
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Organic
Junting Chen, Tobias Ritter
