Article
Chemistry, Multidisciplinary
Sina Rezazadeh, Maxwell I. Martin, Raphael S. Kim, Glenn P. A. Yap, Joel Rosenthal, Donald A. Watson
Summary: The paper reports the nickel-catalyzed alkylation of secondary nitroalkanes using aliphatic iodides to obtain tertiary nitroalkanes. Previously, this method was not feasible due to steric hindrance, but the use of a nickel catalyst in combination with a photoredox catalyst and light overcomes this limitation. The conditions are scalable and tolerant to air and moisture. Importantly, reduction of the resulting tertiary nitroalkanes allows rapid access to alpha-tertiary amines.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Physical
Damien Mahaut, Benoit Champagne, Guillaume Berionni
Summary: In this study, frustrated Lewis pairs were used as catalysts for the hydrogenation of unactivated alkenes with H-2. Ortho-substituted 9-phosphatriptycene derivatives, with weak Lewis basicity and high steric hindrance, were found to be advantageous in catalyzing this reaction in combination with tris(pentafluorophenyl)borane. The protonation of the olefin by the strongly acidic phosphonium cation was identified as the critical step in the reaction.
Article
Multidisciplinary Sciences
Yun-Nian Yin, Rui-Qi Ding, Dong-Chen Ouyang, Qing Zhang, Rong Zhu
Summary: The authors have developed a single-step approach for the synthesis of α-tertiary amides via cobalt-catalyzed intermolecular oxidative hydroamidation of unactivated alkenes. This method shows good selectivity for terminal alkenes and avoids competing reactions with other functional groups, providing a straightforward access to a diverse array of hindered amides.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Roxana Postolache, Juana M. Perez, Marta Castineira Reis, Luo Ge, Esther G. Sinnema, Syuzanna R. Harutyunyan
Summary: In this study, catalytic asymmetric hydrophosphination of α,β-unsaturated carbonyl derivatives using a chiral Mn(I) complex as a catalyst is reported. Various phosphine-containing chiral products can be obtained through H-P bond activation via hydrophosphination of different ketone, ester, and carboxamide-based Michael acceptors.
Article
Chemistry, Organic
Yang Gao, Yushan Cui, Yanping Huo, Jinhong Chen, Minwei She, Xianwei Li, Qian Chen, Xiao-Qiang Hu
Summary: A nickel-catalyzed polarity-reversed hydroamination of olefins has been developed, providing a convenient route to N-alkyl-2-aminobenzophenones intermediates. This method is compatible with a wide range of olefins and anthranils, delivering the desired amines in high yields, making it applicable for organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Tao Li, Ruixin Liu, Xiaojuan Liu, Yaofeng Chen
Summary: In this study, we report a new approach for the synthesis of gem-disilylated alkenes and gem-trisilylated alkanes through a one-pot reaction using organo-calcium complexes as catalysts. Moderate yields of gem-disilylated alkenes and high yields of gem-trisilylated alkanes were obtained. Furthermore, we demonstrate the easy transformation of the synthesized gem-disilylated alkenes into other organosilanes.
Article
Chemistry, Organic
Dengke Li
Summary: The presented method efficiently synthesizes γ-ketoesters using copper catalysis under mild conditions. This strategy can be utilized for the synthesis of biologically active histamine H3 receptor antagonists.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Tianze Zhang, Min Yu, Hanmin Huang
Summary: This study presents an efficient Fe-catalyzed intramolecular isonitrile-olefin coupling reaction for the synthesis of 3-substituted indoles. The protocol features low catalyst loading, mild reaction conditions, and excellent functional group tolerance.
Article
Chemistry, Multidisciplinary
Lingpu Meng, Jingjie Yang, Mei Duan, You Wang, Shaolin Zhu
Summary: Regio- and enantioselective hydroarylamination, hydroalkylamination and hydroamidation of styrenes have been developed using NiH catalysis with a simple bioxazoline ligand under mild conditions. A variety of enantioenriched benzylic arylamines, alkylamines and amides can be easily accessed by employing nitroarenes, hydroxylamines and dioxazolones as amination reagents. Chiral induction in these reactions is proposed to proceed through an enantiodifferentiating syn-hydronickellation step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Leipeng Xie, Jimin Liang, Haohao Bai, Xuanyu Liu, Xiao Meng, Yuan-Qing Xu, Zhong-Yan Cao, Chao Wang
Summary: In this paper, a ligand-controlled, directing-group-assisted strategy was reported to promote NiH-catalyzed site-selective hydroamination of unactivated alkenes. Proper bidentate nitrogen-containing ligands were used to achieve good-to-excellent regioselectivity for the synthesis of 1,1-, 1,2-, and 1,3-diamines from the same substrates. Various O-benzoylhydroxylamine electrophiles with different functional groups can be installed via Ni migration or nonmigration. These protocols provide a method for the enantioselective synthesis of valuable 1,2-diamines and 1,3-diamines.
Article
Chemistry, Multidisciplinary
Julia R. Dorsheimer, Melissa A. Ashley, Tomislav Rovis
Summary: This study reports a new method to activate alpha-3 degrees amines for deaminative arylation by condensing with an electron-rich aldehyde and combining this reactivity with nickel metallaphotoredox to generate benzylic quaternary centers. The reaction is accelerated by added ammonium salts, which inhibit nickel black formation and accelerate the overall reaction rate. The study demonstrates a broad scope of coupling partners and shows an expedited synthesis of ALK2 inhibitors.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Physical
Bryan T. Novas, Rory Waterman
Summary: Organophosphines have attracted attention in various fields, from agriculture to fine chemicals. Hydrophosphination is an efficient method for selectively preparing P-C bonds, maximizing the efficient use of phosphorus. This review provides a comprehensive guide to known catalysts, highlighting advancements in unique substrates and selectivity.
Article
Chemistry, Multidisciplinary
Kentaro Yamakawa, Kana Sakamoto, Takahiro Nishimura
Summary: The enantioselective addition of an imide N-H bond to alkenes has been achieved using a cationic iridium catalyst. Bulky diphosphine ligands were crucial for the reaction, and various substrates including styrene derivatives, allylsilanes, and norbornene gave chiral adducts with high enantioselectivity.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Kentaro Yamakawa, Kana Sakamoto, Takahiro Nishimura
Summary: In this study, enantioselective addition of an imide N-H bond to alkenes was achieved using a cationic iridium catalyst. Bulky diphosphine ligands played a crucial role in the reaction. Various substrates, such as styrene derivatives, allylsilanes, and norbornene, reacted well with alkenes to afford chiral adducts with high enantioselectivity.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Wenchao Chu, Tongliang Zhou, Elwira Bisz, Blazej Dziuk, Roger Lalancette, Roman Szostak, Michal Szostak
Summary: IPr* and CAAC ligands, with their electron-rich properties, have been successfully combined to expand the applications of transition-metal catalysis. These ligands show excellent catalytic performance and flexibility in Cu-catalyzed reactions.
CHEMICAL COMMUNICATIONS
(2022)
