Article
Chemistry, Organic
Ran Song, Zhendong Lian, Wei Feng, Tianyi Guan, Wen Si, Daoshan Yang, Jian Lv
Summary: A novel palladium-catalyzed decarboxylative O-allylation of phenols was developed. A gamma-methylidene-delta-valerolactone (GMDV) was identified as an efficient and selective allylation reagent, leading to the synthesis of allyl phenyl ethers in high yields under mild conditions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Juyeol Lee, Young Ho Rhee
Summary: This study presents a palladium-catalyzed polar inversion reaction where glycals and their isomers can act as nucleophiles. The reaction exhibits high regio- and stereoselectivity in the presence of various aromatic and aliphatic aldehydes, demonstrating its synthetic utility in the concise synthesis of the tetrahydropyran fragment of the anticancer natural product mucocin.
Article
Chemistry, Organic
Gillian Laidlaw, Vilius Franckevicius
Summary: A palladium-catalyzed decarboxylative asymmetric allylic alkylation has been developed for the synthesis of specific compounds, demonstrating potential for medicinal chemistry applications.
Article
Chemistry, Multidisciplinary
Jichao Xiao, Zhenning Li, John Montgomery
Summary: This study demonstrates a method using nickel catalysis and BiOx ligand for the reductive coupling of redox-active esters with aliphatic aldehydes to obtain silyl-protected secondary alcohols. The protocol is simple, mild, and tolerates a variety of functional groups, with potential mechanistic insights pointing towards a radical chain pathway.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Ebbin Joseph, Rafael D. Hernandez, Jon A. Tunge
Summary: Sustainable catalysis: The development of a cobalt-catalyzed decarboxylative allylation of nitrophenyl alkanes, nitroalkanes, and ketones is accomplished. The protocol offers the regioselective synthesis of various allylated products with broad functional group tolerance. Mechanistic studies revealed an unusual activation of Co(II)-salts using new organoreductants.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Magdalena Tasic, Albert Ruiz-Soriano, Daniel Strand
Summary: This article describes a practical three-step approach to diareno[a,e]cyclooctatetraenes using an efficient copper(I) catalyzed double decarboxylation as the key step. The method relies on cheap and abundant reagents, can be performed on scale, and is also applicable to unsymmetrical derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yi An, Mengjuan Wu, Weijian Li, Yaling Li, Zhenzhen Wang, Yansong Xue, Pei Tang, Fener Chen
Summary: The work reported a concise and enantioselective total synthesis of the Schizozygine alkaloid (-)-strempeliopine. A synthetic strategy featuring palladium-catalyzed decarboxylative asymmetric allylic alkylation and diastereoselective Bischler-Napieralski/lactamization was developed to construct the pentacyclic core structure with complete control of four neighbouring stereocenters.
CHEMICAL COMMUNICATIONS
(2022)
Article
Biochemistry & Molecular Biology
Cheng Wang, Shan Yang, Zhibin Huang, Yingsheng Zhao
Summary: This work presents a palladium-catalyzed ortho-selective benzoylation using oxime ether as the directing group and benzoylformic acid as the acyl source. The reaction was carried out with a palladium catalyst and 4CzIPN as the co-catalyst under light. Various non-symmetric benzophenone derivatives were obtained in moderate to good yields.
Article
Chemistry, Multidisciplinary
Yang Zhou, Hang Chen, Panpan Lei, Chunming Gui, Haifeng Wang, Qiongjiao Yan, Wei Wang, Fener Chen
Summary: This article describes a method for palladium-catalyzed allylic substitution using readily available amino acids under mild conditions. The chemoselectivity and multiple allylation can be controlled by adjusting the reaction conditions. This convenient approach allows for the synthesis of valuable N,O-diallylated amino acids with high yields and good functional group tolerance.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Dong-Jin Jang, Sukhyun Lee, Juyeol Lee, Dohyun Moon, Young Ho Rhee
Summary: The study reports a Pd-catalyzed asymmetric addition reaction that leads to the synthesis of beta-substituted ketones in an asymmetric manner through a branch-selective decarboxylative allylation pathway. Various alkoxyallenes as well as amidoallenes can be used in this reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Jun Zheng, Ali Nikbakht, Bernhard Breit
Summary: A dual palladium/photoredox-catalyzed regio- and enantioselective decarboxylative hydroaminoalkylation of allenes with amino acids was reported. This method allows efficient access to protected vinyl 1,2-amino ethers with high levels of branched and enantioselectivity.
Review
Chemistry, Multidisciplinary
Subhabrata Dutta, Trisha Bhattacharya, Daniel B. Werz, Debabrata Maiti
Summary: Allylation reactions, pioneered by Tsuji and Trost, are essential C-C bond-forming transformations with broad applications in synthetic chemistry, bioactive compounds, and pharmaceutical industries. The development of synthetic strategies and the emergence of site-selective C-H activation have further expanded the scope of allylation reactions, eliminating the need for pre-functionalized substrates and activated allylating reagents.
Article
Chemistry, Physical
Sangeth Jenthra, Totan Mondal, Gregor Kemper, Marcus Lantzius-Beninga, Markus Hoelscher, Walter Leitner
Summary: A highly chemo- and regioselective decarboxylative Heck-type coupling of carboxylic acids and terminal olefins was achieved using a catalytic system composed of Pd(OAc)(2) in the presence of phosphine-sulfonamido ligands. The bulky ligand L1 favored the formation of 1,1-disubstituted branched olefins with high selectivity, while the less bulky ligand L2 resulted in the formation of 1,2-disubstituted linear products in high yield. Detailed mechanistic investigation revealed that the aryl substituent at the sulfonamide group of ligand L1 favored 1,2-insertion, while the less bulky ligand L2 favored 2,1-insertion.
Article
Chemistry, Organic
Ashok Donthoju, Anandarao Munakala, Sushma Ellandula, Rambabu Chegondi
Summary: In this study, we have reported a palladium(0)-catalyzed decarboxylative oxa-Michael addition/remote alpha-allylation/1,3-migration reaction with high yields. The reaction is triggered by a base-mediated retro-Michael ring-opening reaction and subsequent syn-selective oxa-Michael addition.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xian-Xiao Chen, Hao Luo, Ye-Wei Chen, Yang Liu, Zhi-Tao He
Summary: Chain walking has been an efficient method for the functionalization of inert C(sp(3))-H bonds, but it has limitations on mono-olefin migration and functionalization. In this study, we demonstrate the feasibility of tandem directed simultaneous migrations of remote olefins and stereoselective allylation. The use of palladium hydride catalysis and secondary amine morpholine as a solvent is crucial for achieving high substrate compatibility and stereochemical control.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Lin-Lin Zhang, Bing-Chao Da, Shao-Hua Xiang, Shuai Zhu, Zi-Yun Yuan, Zhen Guo, Bin Tan
Article
Multidisciplinary Sciences
Lei Zhang, Shao-Hua Xiang, Jun (Joelle) Wang, Jian Xiao, Jun-Qi Wang, Bin Tan
NATURE COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Yong-Bin Wang, Quan-Hao Wu, Zhi-Peng Zhou, Shao-Hua Xiang, Yuan Cui, Peiyuan Yu, Bin Tan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Organic
Dong-Liang Lu, Ye-Hui Chen, Shao-Hua Xiang, Peiyuan Yu, Bin Tan, Shaoyu Li
Correction
Multidisciplinary Sciences
Lei Zhang, Shao-Hua Xiang, Jun (Joelle) Wang, Jian Xiao, Jun-Qi Wang, Bin Tan
NATURE COMMUNICATIONS
(2019)
Article
Multidisciplinary Sciences
Shuai Zhu, Ye-Hui Chen, Yong-Bin Wang, Peiyuan Yu, Shao-Yu Li, Shao-Hua Xiang, Jun-Qi Wang, Jian Xiao, Bin Tan
NATURE COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Shengyi Yan, Wang Xia, Shaoyu Li, Qiuling Song, Shao-Hua Xiang, Bin Tan
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Correction
Chemistry, Multidisciplinary
Shengyi Yan, Wang Xia, Shaoyu Li, Qiuling Song, Shao-Hua Xiang, Bin Tan
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Review
Chemistry, Multidisciplinary
Jun Kee Cheng, Shao-Hua Xiang, Shaoyu Li, Liu Ye, Bin Tan
Summary: Atropisomerism is a stereochemical behavior exhibited by three-dimensional molecules with rotationally restricted sigma bonds, and compounds with atropisomerically chiral properties are increasingly utilized in fields where molecular asymmetry is influential. There is a steady demand for atroposelective synthesis, leading to conceptually novel and streamlined methods for expanding the structural diversity of atropisomers. This review summarizes key achievements in the stereoselective preparation of biaryl, heterobiaryl, and nonbiaryl atropisomers between 2015 and 2020, emphasizing synthetic strategies for each structural class and potential applications of atropochiral targets.
Article
Chemistry, Multidisciplinary
Jian Zhang, Jun Wei, Wei-Yi Ding, Shaoyu Li, Shao-Hua Xiang, Bin Tan
Summary: Pnictogen-bonding catalysis based on sigma-hole interactions has been the focus of attention for synthetic chemists. A novel chiral antimony cation/anion pair was utilized to catalyze the enantioselective transfer hydrogenation of benzoxazines with remarkable efficiency and enantiocontrol potency even at 0.05 mol % loading. Investigation into the properties of the catalyst and mechanistic insights were conducted through nonlinear effect studies, 1H NMR, LC-MS, and control experiments.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Junxian Yang, Ji-Wei Zhang, Wen Bao, Sheng-Qi Qiu, Shaoyu Li, Shao-Hua Xiang, Jun Song, Junmin Zhang, Bin Tan
Summary: This study reports a new strategy for catalytic enantioselective construction of axially chiral B-aryl-1,2-azaborines, achieving efficient stereochemical control through multiple hydrogen bonding interactions. The reaction demonstrates high efficiency, excellent enantioselectivity, shortened reaction duration, and high practicality with scalable reaction and facile cleavage of N-N bond in the product.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Multidisciplinary
Jun Kee Cheng, Shao-Hua Xiang, Bin Tan
Summary: This paper describes the strategies to address the challenges in efficient synthetic access and skeletal variety within the organocatalytic context. The approaches include modulating nucleophilicity, designing electron-withdrawing activating groups, and using electrophilic arene precursors for arylation. These strategies have led to the synthesis of structurally diverse axially chiral compounds.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Pengquan Chen, Mei-Jun Lv, Jun Kee Cheng, Shao-Hua Xiang, Xiang-Zhong Ren, Junmin Zhang, Bin Tan
Summary: Azonaphthalenes have been confirmed as effective arylation reagents for various asymmetric transformations. In this study, a highly efficient approach to form triaryl-substituted all-carbon quaternary stereocenters through chiral phosphoric acid-catalyzed enantioselective arylation of 3-aryl-2-oxindoles with azonaphthalenes is revealed. This chemistry is scalable and demonstrates excellent functional group tolerance, providing a series of 3,3-disubstituted 2-oxindole derivatives in good yields with excellent enantiocontrol.
Article
Chemistry, Multidisciplinary
Si-Li Lin, Ye-Hui Chen, Huan-Huan Liu, Shao-Hua Xiang, Bin Tan
Summary: In this study, chiral cyclobutene units were synthesized using bicyclo[1.1.0]butanes for the first time, offering an efficient and asymmetric route with good regio- and enantiocontrol. Control experiments verified the formation of a key carbocation intermediate at the benzylic position.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Physical
Liang-Wen Qi, Shaoyu Li, Shao-Hua Xiang, Jun (Joelle) Wang, Bin Tan
