Article
Chemistry, Organic
Daiya Kase, Ryosuke Haraguchi
Summary: This study presents a fluoride-mediated nucleophilic aromatic amination of chloro-1H-1,2,3-triazolium salts with aliphatic amines, yielding amino-1,2,3-triazolium salts with various functional groups that have the potential for further transformations. Additionally, the transformation of an amino-1,2,3-triazolium salt into an N-heterocyclic imine (NHI) was found to exhibit excellent catalytic activity for the cyanosilylation of acetophenone with trimethylsilyl cyanide.
Article
Chemistry, Organic
Nidhi Mishra, Sumit K. Singh, Anoop S. Singh, Anand K. Agrahari, Vinod K. Tiwari
Summary: Glycosyl triazoles are efficient ligands for Cu-catalyzed Sonogashira reaction, overcoming challenges of sideways homocoupling reactions. High product yields can be achieved at 130 degrees C for various substrates, showing versatility of this catalytic system.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Long Zheng, Xueying Guo, Ying-Chao Li, Yichen Wu, Xiao-Song Xue, Peng Wang
Summary: In this study, the coupling of alkynes with Fischer-type copper carbene species bearing an alpha-siloxyl group is reported. The copper carbene species can be in situ generated from acylsilanes under photoirradiation and redox-neutral conditions. The side-arm modified bisoxazoline (SaBox) ligands play a crucial role in this coupling reaction, providing the corresponding alkynyl alcohol in high yields with remarkable heterocycle tolerance and broad substrate scope.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Multidisciplinary Sciences
Bo Yang, Shaodong Lu, Yongdong Wang, Shifa Zhu
Summary: In this study, the authors demonstrated a photoredox-catalyzed synthesis of C2-linked molecules using gaseous acetylene under mild conditions. The strategy not only enables the formation of two new C-C bonds, but also creates two C-H bonds in mechanistically distinct ways, offering a reliable and safe approach for incorporating acetylene into fine chemicals.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Tairan Cheng, Boxiang Liu, Rui Wu, Shifa Zhu
Summary: This study reported a copper-catalyzed three-component carboboration reaction using B(2)Pin(2) and Michael acceptors with acetylene, resulting in cis-alkenyl boronates bearing a homoallylic carbonyl group. The reaction was robust and could be performed on the molar scale, and the resulting products could be easily converted into diverse functionalized molecules.
Article
Chemistry, Multidisciplinary
Weiguang Yang, Yu Zhao, Zitong Zhou, Li Li, Liao Cui, Hui Luo
Summary: 1,2-Substituted benzimidazoles were synthesized by stirring a mixture of copper catalysts, N-substituted o-phenylenediamines, sulfonyl azides, and terminal alkynes. The intermediate N-sulfonylketenimine underwent two nucleophilic additions and elimination of the sulfonyl group via cyclization, with sulfonyl azides and copper catalysts activating the terminal alkynes for benzimidazole synthesis.
Article
Chemistry, Organic
Shuai Liu, Yi-Sen Qian, Jian-Lin Xu, Lei Xu, Yun-He Xu
Summary: A three-component coupling method was reported for the regio- and stereoselective difunctionalization of allenes with allenyl ethers, bis(pinacolato)diboron, and gem-dichlorocyclobutenones as electrophiles, leading to highly functionalized cyclobutenone products tethering with an alkenylborate fragment. The polysubstituted cyclobutenone products also showed diverse transformation abilities.
Article
Chemistry, Multidisciplinary
Mamata Maiti, Sayan K. K. Jana, Biplab Maji
Summary: The first example of asymmetric alkene-alkene reductive coupling is demonstrated using visible-light-fueled photoredox/cobalt dual catalysis. The desymmetrization reaction achieves single-step operation with high yields (up to 95%) and excellent control of both relative (>99 : 1 dr) and absolute stereochemistry (up to 98 : 2 er), generating products with up to five chiral centers. Preliminary mechanistic investigations suggest key steps involving light-mediated controlled low-valent cobalt complex generation, oxidative ene-ene cyclization, and protonation.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Xianjun Xu, Huangdi Feng, Erik V. Van der Eycken
Summary: An efficient synthesis route for unsymmetric 1,4-diamino-2-butynes has been developed using a microwave-assisted Cu(I)-catalyzed cross-A(3)-coupling/decarboxylative coupling process. The multicomponent reaction yields target products in moderate to good yields with high chemoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Polymer Science
Ying Wang, Linlin Zhu, Wenhao Chen, Zhi Zhou, Zhen Zhang, Nikos Hadjichristidis
Summary: A highly efficient and multicomponent step-growth polymerization via carbene intermediates is established by bimetallic relay catalytic systems. This method overcomes the limitation on the choice of carbene monomers and achieves high-molecular-weight polymers. The results suggest an untapped pathway for the use of metal carbene intermediates to construct new macromolecules.
Article
Chemistry, Organic
Wanjun Chen, Yaping Cheng, Tao Zhang, Yu Mu, Wenqi Jia, Guodu Liu
Summary: A nickel-catalyzed stereoselective asymmetric intramolecular reductive coupling of N-1,6-alkynones was reported, achieving efficient synthesis of versatile functionalized chiral pyrrolidines with high yields, excellent stereoselectivity, and enantioselectivity. The developed reaction is applicable to a broad substrate scope and can be scaled up to gram scale without loss of enantioselectivity. The study also investigated ligand effects and reaction mechanism, suggesting wider applications in organic synthesis and chemical biology, and potential for further explorations in new research fields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Yigao Tao, Rong Hu, Xiaoming Jie, Weiping Su
Summary: A silver oxidant/Lewis acid catalyst was used to promote a three-component carbo-heterofunctionalization reaction of alkenes. The reaction involved the addition of nucleophiles and 1,3-dicarbonyl compounds, resulting in the difunctionalization of styrene derivatives. Mechanistic investigations revealed that the silver complex oxidizes the radical intermediate, leading to the formation of carbocation intermediates and contributing to the high yields and selectivity of the reaction.
Article
Chemistry, Multidisciplinary
Yiqiong Zhang, Bo Zhou, Zengxi Wei, Wang Zhou, Dongdong Wang, Jing Tian, Tehua Wang, Shuangliang Zhao, Jilei Liu, Li Tao, Shuangyin Wang
Summary: This study presents a novel and efficient hydrogen production system combining glucose-assisted Cu(I)/Cu(II) redox with HER, achieving lower electricity consumption and higher production efficiency.
ADVANCED MATERIALS
(2021)
Article
Chemistry, Multidisciplinary
James E. Baumann, Gojko Lalic
Summary: A new method for the differential dihydrofunctionalization of terminal alkynes has been developed, enabling the synthesis of allylic boronate esters through a reductive three-component coupling reaction. This transformation, promoted by a copper/palladium catalyst system, hydrofunctionalizes both pi-bonds of the alkyne. The method is compatible with a wide range of functional groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jian Rong, Yidan Wu, Xiaoheng Ji, Tingting Zhao, Bangshao Yin, Yutao Rao, Mingbo Zhou, Atsuhiro Osuka, Ling Xu, Jianxin Song
Summary: In the presence of AlCl3, the reaction between meso-formyl Ni(II) porphyrin 1 and zirconacyclopentadiene 2 yielded four products 3, 4, 5, and 6 with a total yield of over 85%. The structures of these compounds were well-characterized, and the mechanism of their formation was proposed based on isotopic labeling experiments, suggesting the involvement of a Friedel-Crafts-type reaction and beta-H shift.
