Article
Chemistry, Applied
Alexander A. A. Fadeev, Gabriele Manca, Martin Kotora
Summary: A synthesis of 1,4-diborylated benzenes from alkynes and ethynyl boronate was achieved using Ru-catalyzed regioselective co-cyclotrimerization. The reaction showed good applicability to alkynes with metal-coordinating groups, giving useful diborylated benzenes in modest yields. DFT calculations provided insights into the reaction mechanism and the reason for its remarkable regioselectivity. Selected diborylated benzenes were further transformed into various products, including natural bioactive small molecules like quinones and hydroquinones.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Martin Berger, Davide Carboni, Paolo Melchiorre
Summary: The study presents the first catalytic enantioselective conjugate addition of allyl groups to alpha, beta-unsaturated aldehydes, utilizing the visible-light-excitation of chiral iminium ions to activate allyl silanes toward the formation of allylic radicals. This radical mechanism overcomes issues seen in traditional conjugate allylation processes and selectively installs prenyl fragments at the beta-carbon of enals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Applied
Seoung-Mi Choi, Ju Hyun Kim
Summary: This review summarizes the progress made in the synthesis of 2H-pyrroles since 2000, including methods such as dearomatization of 1H-pyrrole, oxidation of pyrrolines or pyrrolidines, ring construction via catalytic cycloaddition, and rearrangement of 3H-pyrroles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Haripriyo Mondal, Subimal Patra, Shuvendu Saha, Tarak Nayak, Uddalak Sengupta, Modhu Sudan Maji
Summary: Chlorination plays a crucial role in drug discovery and development by altering the physiological characteristics of bioactive compounds. However, certain functional groups limit the reactivity of chlorination reactions. This study introduces a new catalyst for late-stage halogenation of peptides and drugs, which shows high functional-group tolerance and compatibility with diverse compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Chun-Lin Zhang, Yuan-Yuan Gao, Hai-Ying Wang, Bang-An Zhou, Song Ye
Summary: An NHC-catalyzed de novo synthesis method for axially chiral benzothiophene/benzofuran-fused biaryls has been reported, providing a convenient and efficient access to these compounds with high enantioselectivities. The method also works well for the synthesis of tetra-ortho-substituted biaryls, addressing an unsolved problem in the field.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Wing-Hin Ng, Ying-Pong Lam, Rong-Bin Hu, Wing-Lok Ng, Ying-Yeung Yeung
Summary: This study presents a novel method for synthesizing glycinamides through a zwitterion-catalyzed aminobromination reaction. This method avoids harsh conditions and provides an efficient synthetic route for producing glycinamides.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Meiyun Su, Lina Guo, Peiyu Mao, Meng Xiao, Wenjie Liu, Shaohua Wang
Summary: The catalyst-free electrochemical halogenation and trifluoromethylation of 4H-pyrido[1,2-a]pyrimidin-4-ones was successfully achieved under external-oxidant-free conditions. This strategy provides an easy and green approach for the synthesis of functionalized new 4H-pyrido[1,2-a]pyrimidin-4-one derivatives with broad scope, good functional group tolerance, and high regioselectivity.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Manoj K. Jaiswal, Abhishek Gupta, Mangal S. Yadav, Vinay K. Pandey, Vinod K. Tiwari
Summary: A novel organocatalyzed [3+2] cycloaddition reaction has been developed for the construction of 1,5-disubstituted triazolyl glycoconjugates. The reaction involves the use of Schreiner thiourea organocatalysts to activate nitroolefins through double hydrogen bonding. This metal-free and acid-free synthetic protocol is operationally simple, regioselective, and complements the classical RuAAC catalyzed synthesis of 1,5-disubstituted 1,2,3-triazoles. By using catalytic amounts of the Schreiner thiourea organocatalyst, a wide range of organic azides can react with nitroolefins to produce diverse 1,5-disubstituted 1,2,3-triazoles in good yields with excellent regioselectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Stefanie Mayr, Hendrik Zipse
Summary: The relative rates of Lewis base-catalyzed acylation of aryl-substituted 1,2-diols with anhydrides of varying sizes have been determined. Depending on the anhydride reagent structure, the secondary hydroxyl group of the 1,2-diol reacts faster than the primary one. This preference is further enhanced in the second acylation step from monoesters to diesters through size and additional steric effects. The first acylation step is found to be up to 35 times faster than the second one for primary alcohols due to neighboring group effects.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Applied
Shengshu Liu, Bing-Qian Zhang, Wen-Ying Xiao, Yin-Long Li, Jun Deng
Summary: Heterocycles containing halogen or chalcogen elements are crucial building blocks in natural products and bioactive targets. Catalytic asymmetric functionalization of carbon-carbon unsaturated bonds with halogen or chalcogen electrophiles is an efficient method to obtain chiral heterocyclic backbones.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Yanxia Lv, Zhong-Wei Hou, Pinhua Li, Lei Wang
Summary: A site-selective electrochemical C-H bromination of (hetero)arenes with 2-bromoethan-1-ol through paired electrolysis is developed, where the anodic oxidation of Br- produced by the cathodic reduction of 2-bromoethan-1-ol is essential. The method shows good compatibility with common functional groups and can be easily scaled up. A variety of brominated products can be obtained with satisfactory yields at room temperature in a simple undivided cell.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Ryuichi Nishiyori, Megumi Okada, John R. J. Maynard, Seiji Shirakawa
Summary: This study demonstrated the successful development of highly enantioselective bromolactonizations of 4-aryl-4-pentenoic acids using BINOL-derived chiral bifunctional sulfide catalysts, highlighting the importance of the bifunctional design in chiral sulfide catalysts. The catalytic asymmetric reaction system could also be applied to highly stereoselective desymmetrizing bromolactonizations, showing promising potential for further applications in asymmetric synthesis.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Haiyan Xu, Lanping Hu, Guanghua Zhu, Yueping Zhu, Yang Wang, Zheng-Guang Wu, You Zi, Weichun Huang
Summary: A simple and practical method for synthesizing aromatic halides has been developed using the Lewis base DABCO as a catalyst. This method proceeds conveniently and efficiently at ambient conditions, providing the desired products in good to excellent yields and selectivity.
Article
Chemistry, Applied
Alexander Garay-Talero, Paola Acosta-Guzman, Diego Gamba-Sanchez
Summary: This manuscript presents a regioselective chlorination of arenes, yielding almost exclusively the monochlorinated product. It tolerates a wide range of functional groups and substituted aromatic rings, and demonstrates the utilization of chlorosulfonium salts as the chlorinating agent, avoiding the formation of organic byproducts.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Hongliang Zhao, Chao-Yue Zhao, Lili Chen, Chungu Xia, Xin Hong, Senmiao Xu
Summary: We report the iridium-catalyzed enantioselective C-H borylation of aryl chlorides, which could afford axially chiral biaryls with high enantioselectivities. The method demonstrates high turnover number (TON) and shows potential for synthetic applications in C-B, ortho-C-H, and C-Cl bond functionalization.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
