Article
Chemistry, Multidisciplinary
Terry Shing-Bong Lou, Yu Kawamata, Tamara Ewing, Guillermo A. Correa-Otero, Michael R. Collins, Phil S. Baran
Summary: Simple access to aryl sulfinates from aryl iodides and bromides is achieved using an inexpensive Ni-electrocatalytic protocol. The reaction demonstrates broad scope, scalability, and use of a stock solution of simple SO2 as the sulfur source, and is compared to state-of-the-art Pd-based methods to highlight its limitations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Xiaoyuan Ying, Yuxi Li, Luyang Li, Chao Li
Summary: A general Ni-catalyzed C(sp(2))-I selective cross-electrophile coupling (XEC) reaction has been developed for the construction of arene-flanked quaternary carbons. This reaction exhibits excellent C(sp(2))-I selectivity and functional group compatibility, and enables the synthesis of medicinally relevant and synthetically challenging compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jean-Marc I. A. Lawrence, Paul E. Floreancig
Summary: This work presents a method for electrochemical oxoammonium ion regeneration by understanding the relationship between intermediate cation stability and reaction kinetics, which can expand the scope of electrocatalysis.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
John E. A. Russell, Sharon R. Neufeldt
Summary: The chemoselective cross-coupling of phenol derivatives is valuable for synthesizing products with retained halides. This review focuses on recent developments in selective cross-couplings of chloroaryl phenol derivatives, particularly reactions involving chloroaryl tosylates. A detailed discussion is provided on the first example of a C-O-selective Ni-catalyzed Suzuki-Miyaura coupling of chloroaryl tosylates.
Review
Chemistry, Multidisciplinary
Binlin Zhao, Baskaran Prabagar, Zhuangzhi Shi
Summary: C-H functionalization is a fast and atom-economical approach for synthesizing complex molecules, beneficial for late-stage modifications. Modern strategies allow cleavage of less reactive bonds to form essential links, highlighting renewable and sustainable features.
Article
Chemistry, Organic
Ranran Cui, Yinqi Wang, Liyan Yuwen, Li Gao, Zhuo Huang, Wei-Han Wang, Qing-Wei Zhang
Summary: In this study, a novel Ni(II)-catalyzed asymmetric C-P cross-coupling reaction is developed for the synthesis of valuable chiral heterocyclic tertiary phosphine oxides. The method is mild, efficient, and does not require an external reductant, light irradiation, or electricity.
Article
Chemistry, Multidisciplinary
Chuanyong Wang, Xiaobo Hu, Cheng Xu, Qiangqiang Ge, Qingliang Yang, Jianqi Xiong, Wei-Liang Duan
Summary: A novel nickel-catalyzed enantioselective C(sp(2))-P cross-coupling has been developed for the synthesis of P-stereogenic phosphine oxides. The reaction of racemic secondary phosphine oxides with alkenyl/aryl bromides produces P-stereogenic phosphine oxides with high yields and enantioselectivities. The method shows excellent tolerance towards various functional groups and has been applied for late-stage functionalization and product transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Jiantao Fu, Windsor Lundy, Rajdip Chowdhury, J. Cameron Twitty, Long P. Dinh, Jessica Sampson, Yu-hong Lam, Christo S. Sevov, Mary P. Watson, Dipannita Kalyani
Summary: An electrochemical, nickel-catalyzed reductive coupling between alkylpyridinium salts and aryl halides is described. High-throughput experimentation (HTE) was used for rapid optimization and evaluation of various pharmaceutically relevant aryl halides, including complex drug-like substrates. The transformation is compatible with both primary and secondary alkylpyridinium salts with different conditions. Mechanistic insights were crucial for improving the efficiency of coupling using secondary alkylpyridinium salts. Systematic comparisons between electrochemical and non-electrochemical methods revealed the complementary scope and efficiency of the two approaches.
Article
Chemistry, Physical
Kaituo Dong, Cristofer Pezzetta, Qiu-Cheng Chen, Alexander Kaushansky, Amedeo Agosti, Giacomo Bergamini, Robert Davidson, Lilac Amirav
Summary: Carbon-heteroatom cross-coupling reactions are important for industrial chemical processes, especially for the synthesis of pharmaceuticals, agrochemicals, and biologically active compounds. Photocatalyst/transition metal dual catalytic systems, using semiconductor nanoparticles as heterogeneous light sensitizers, offer advantages such as low-cost production, tunable photophysical properties, easy separation, high photostability, and recyclability. The combination of CdSe@CdS nanorod photocatalysts with a Ni complex catalyst enables efficient selective light-induced C-O cross-coupling reactions, achieving high yield and impressive turnover numbers.
Article
Chemistry, Organic
Yang Wang, Feng Zhang, Yi Wang, Yi Pan
Summary: This work describes an electrochemical enabled nickel-catalyzed chemoselective C-S bond coupling protocol for the production of aryl sulfides and sulfones. By simply switching the nickel catalysts and electrodes, this electrochemical C-S bond coupling has demonstrated excellent redox activity, scalability, and sustainability. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Taline Kerackian, Didier Bouyssi, Guillaume Pilet, Maurice Medebielle, Nuno Monteiro, Julien C. Vantourout, Abderrahmane Amgoune
Summary: This article describes the development and in-depth study of a cross-electrophile coupling of alkyl N-acyl imides with alkyl halides using nickel catalysis and electrochemistry. The method utilizes the stability and easy access of N-acyl imides to selectively synthesize dissymmetric dialkyl ketones. Mechanistic studies reveal the generation of alkyl radicals through single-electron oxidation of alkyl bromides by electrogenerated (bpy)Ni(I) species. The reaction of alkyl N-acyl imides with (bpy)Ni(0) and (bpy)Ni(I) species leads to Ni(II) acyl intermediates. A comprehensive mechanistic picture of this selective cross-electrophile coupling is achieved through these investigations.
Article
Chemistry, Organic
Soumya Mondal, Subal Mondal, Siba P. Midya, Suman Das, Sahidul Mondal, Pradyut Ghosh
Summary: In this study, a novel merged photocatalytic pathway is demonstrated for the C-O cross-coupled esterification of carboxylic acids to alpha-oxycarbonyl-beta-ketones. Decarboxylation of alpha,beta-unsaturated acids promotes the formation of the beta-ketone fragment in the desired product. Water serves as the oxygen source for the ketone segment, while aerial oxygen acts as an oxidant, making this synthetic methodology environmentally friendly and sustainable. The cascade reaction occurs under a dual Ir/Pd-catalytic pathway, resulting in the liberation of H2O and CO2 as the only byproducts.
Article
Chemistry, Organic
Soumya Mondal, Subal Mondal, Siba P. Midya, Suman Das, Sahidul Mondal, Pradyut Ghosh
Summary: Here, the first merged photocatalytic pathway for the C-O cross-coupled esterification of carboxylic acids to aoxycarbonyl-ss-ketones has been demonstrated. The decarboxylation of α,ss-unsaturated acids promotes the formation of the ss-ketone fragment of the desired product. This methodology utilizes water as the source of oxygen for the ketone segment and aerial oxygen as an oxidant, making it a green and sustainable synthetic approach.
Article
Chemistry, Organic
Yuqiang Li, Guoyin Yin
Summary: The nickel-catalyzed Ullmann cross-coupling reported in this study displays high cross-selectivity and chemoselectivity, making it applicable to a wide range of functional groups.
Article
Multidisciplinary Sciences
Yantao Li, Qianzhen Shao, Hengchi He, Chengjian Zhu, Xiao-Song Xue, Jin Xie
Summary: The authors present a method to synthesize tetrasubstituted olefins via dual photo- and nickel catalysis under an air atmosphere, without the need for an inert atmosphere. The synthesis of these compounds under mild conditions is challenging, but the authors were able to achieve it by using readily available carboxylic acids and alkenyl triflates. The method shows promise for applications in complex molecule modification and gram-scale synthesis.
NATURE COMMUNICATIONS
(2022)