Article
Chemistry, Organic
Bei Wei, Kaikai Dong, Jingyang Zhang, Liansuo Zu
Summary: This study introduces a mild synthetic method for producing 4aH-carbazole intermediates with significant flexibility and variability, which can be further rearranged into carbazoles. It enriches the chemistry of 4aH-carbazoles and provides a consecutive rearrangements approach for precise decoration of the inert carbazole ring.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Mikhail Feofanov, Vladimir Akhmetov, Ryo Takayama, Konstantin Amsharov
Summary: A facile synthesis of N-arylated carbazoles via ladderization of fluorinated oligophenylenes is described, involving two subsequent nucleophilic substitutions triggered by an electronic transfer from dimsyl anions. The reaction allows effective one-pot formation of at least six C-N bonds with pronounced selectivity to the C-F bond placement.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Zheng-Lin Wang, Yun-Hao Zhang, Jun-Yu Huang, Jian Zhou, Ya-Qin Yu, Dexin Feng, Da-Zhen Xu
Summary: The development of aerobic oxidative C-H/N-H cross-coupling catalyzed by first-row transition metals, particularly iron, is challenging but attractive. In this study, a first iron-catalyzed intramolecular cross-dehydrogenative coupling was reported for the synthesis of carbazoles and indoles using air as the oxidant. The protocol offers a general and efficient method for C-N bond formation with excellent functional group compatibility and provides a wide range of N-H carbazoles and indoles in good yields. Remarkably, all carbazoles are prepared through a C-H amination and aromatization process with the loss of 6Hs from 2-cyclohexenyl aminoarenes. Furthermore, the method also works for C-O bond formation.
Article
Chemistry, Applied
Li He, Yongjun Xu
Summary: An intramolecular C-H amination for the synthesis of carbazoles with a Pd(II)/TBPB system has been developed. This method forms carbazole products in good to excellent yields. Notably, the use of water as solvent in this catalytic process is also effective.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Rakesh K. Saunthwal, Maria Schwarz, Rajendra K. Mallick, William Terry-Wright, Jonathan Clayden
Summary: A practical method for enantioselective synthesis of alpha,alpha-diarylmethylamines without using transition metals is achieved through asymmetric alpha-arylation of benzylamines. Enantioselective lithiation of N '-aryl-N-benzyl-N-isopropyl ureas using a chiral lithium amide base generates benzyllithium, which undergoes a stereospecific intramolecular nucleophilic aromatic substitution to form the urea derivative of alpha,alpha-diarylmethylamine with ee up to >99%. Acid treatment induces an azatropic shift with retention of configuration, allowing hydrolysis to yield the target amine.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Wenchao Gao, Luyi Zong, Weilong Wu, Ming Zhu, Wenmin Liu, Yiyang Zhao, Ting Li, Sheng Zhang
Summary: A new method was developed to construct cyclic phosphinamides with various functional groups under mild conditions via an intramolecular electrochemical C-H phosphinamidation process. This method also provided an alternative route to organic electroluminescent materials and P-N ligands.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Shihao Cheng, Ruihan Zhao, Chenhu Dong, Yong Ling, Yu Zhao
Summary: A ring distortion strategy was used to synthesize a series of intramolecular cross-coupled analogues of forskolin. The target compounds were obtained through several reaction steps with high yields.
Article
Chemistry, Organic
Wenchao Gao, Luyi Zong, Weilong Wu, Ming Zhu, Wenmin Liu, Yiyang Zhao, Ting Li, Sheng Zhang
Summary: A new method for constructing six-membered cyclic phosphinamides without oxidants and transition metals has been developed, providing a new pathway for organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yu-Zhen Zhang, Meng-Meng Xu, Xu-Ge Si, Jun-Li Hou, Quan Cai
Summary: An efficient approach for the enantioselective synthesis of inherently chiral calix[4]arenes via palladium-catalyzed asymmetric intramolecular C-H arylations is reported. The use of a chiral bifunctional phosphine-carboxylate ligand successfully induced inherent chirality on macrocyclic scaffolds, resulting in a wide range of calix[4]arenes with fluorenone motifs obtained with good yields and excellent enantioselectivities. Diverse transformations of the products demonstrate the synthetic utility of this method, substantially expanding the chemical space of chiral calix[4]arenes. Investigations of photophysical and chiroptical properties reveal the great potential of inherent chirality in the development of organic optoelectronic materials for calix[4]arenes bearing two fluorenone moieties.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Ian A. Pocock, Alya M. Alotaibi, Kesar Jagdev, Connor Prior, Gregory R. Burgess, Louise Male, Richard S. Grainger
Summary: Carbazoles are commonly used for their photophysical and electronic properties, but the functionalization at the bay (4,5-) position has been challenging. A simple methodology has been reported to introduce versatile 4,5-functionality, enabling further exploration of ring annulation and proximity effects on carbazole properties.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Lei Wang, Shuaijie Wu, Shuting Zhang, Qianqian Hu, Qiang Wang, Jing Sun, Ying Han, Chao-Guo Yan
Summary: A highly efficient palladium-catalyzed allenamide allylic alkylation of sulfenate anions under mild conditions is demonstrated, providing a practical protocol to access various sulfoxide-containing heterocyclic compounds. The transformation features a broad substrate scope, good functional group tolerance, easy scalability, and convenient synthetic transformation.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jiateng Wang, Mengxia Liu, Yue Zhang, Gehua Bi, Yi Zhao, Kai Yang, Xin Huang
Summary: A switchable and benign protocol has been developed for the chemo-selective synthesis of sulfoxides and alpha-alkoxy-beta-ketothioethers. By regulating the reaction temperature, various thiophenols and alkenes/alkynes were found to be compatible for achieving the target compounds in medium to high yields. In particular, methanol not only acted as a solvent but also participated in the reaction process as a hydrogen donor. The study also demonstrated that Selectfluor is an efficient multifunctional reagent in the reaction system.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Shyamal Kanti Bera, Palash J. Boruah, Shraddha Saraswati Parida, Amit K. Paul, Prasenjit Mal
Summary: This study presents a new method for direct photochemical dehydrogenative C-N coupling, in which the reaction energy is reduced by the N-H···π interaction.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Biao Zhang, Junhao Ruan, Daniel Seidel, Weijie Chen
Summary: Unprotected cis-2,3-diarylpiperidines are synthesized through a palladium-catalyzed cross-coupling reaction between aryl halides and endocyclic 1-azaallyl anions. These intermediates are generated in situ by the deprotonation of 2-aryl-1-piperideines, precursors that are readily prepared from simple piperidines. An asymmetric version of this reaction provides products with moderate to good yields and enantioselectivities when using (2R, 3R)-iPr-BI-DIME as the ligand. This study expands the synthetic utility of endocyclic 1-azaallyl anions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Qingqing Wang, Xiaojing Zhang, Pan Wang, Xinlong Gao, Heng Zhang, Aiwen Lei
Summary: The synthesis of carbazoles was achieved through electrochemical Pd-catalyzed intramolecular C-H amination of 2-amidobiaryls under mild conditions, without the need for external chemical oxidants. The resulting carbazoles are easily scalable and modifiable, providing a simple and sustainable method for their construction compared to previous techniques.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ariel L. Cappelletti, Paula M. Uberman, Sandra E. Martin, Martin E. Saleta, Horacio E. Troiani, Rodolfo D. Sanchez, Raul E. Carbonio, Miriam C. Strumia
AUSTRALIAN JOURNAL OF CHEMISTRY
(2015)
Article
Chemistry, Organic
Gisela J. Quinteros, Paula M. Uberman, Sandra E. Martin
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
Walter D. Guerra, Roberto A. Rossi, Adriana B. Pierini, Silvia M. Barolo
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Walter D. Guerra, Maria E. Buden, Silvia M. Barolo, Roberto A. Rossi, Adriana B. Pierini
Article
Chemistry, Multidisciplinary
Paula M. Uberman, Carolina S. Garcia, Julieta R. Rodriguez, Sandra E. Martin
Article
Chemistry, Organic
Maria E. Buden, Javier I. Bardagi, Marcelo Puiatti, Roberto A. Rossi
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Catalina Biglione, Ariel L. Cappelletti, Miriam C. Strumia, Sandra E. Martin, Paula M. Uberman
JOURNAL OF NANOPARTICLE RESEARCH
(2018)
Article
Chemistry, Medicinal
Maria Matilde Ramirez Moran, Jorge Eduardo Angel Guio, Natividad Herrera Cano, Biagina del Carmen Migliore, Rodolfo Izquierdo, Jaime Charris, Simon Lopez, Anita Israel, Ana Santiago, Roberto Rossi, Luis Perdomo, Akram Samear Dabian, Mariagracia Vera Sosa, Alejandra Villalba, Ligia Biagina Angel Migliore
LETTERS IN DRUG DESIGN & DISCOVERY
(2018)
Article
Chemistry, Organic
Walter D. Guerra, Roberto A. Rossi, Adriana B. Pierini, Silvia M. Barolo
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Review
Chemistry, Organic
Paula M. Uberman, Sandra E. Martin
CURRENT ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Cherif Adouama, Maria E. Buden, Walter D. Guerra, Marcelo Puiatti, Benoit Joseph, Silvia M. Barolo, Roberto A. Rossi, Maurice Medebielle
Article
Construction & Building Technology
Melina Gomez, Lucas Ernesto Peisino, Jeronimo Kreiker, Rosana Gaggino, Ariel Leonardo Cappelletti, Sandra E. Martin, Paula M. Uberman, Maria Positieri, Barbara Belen Raggiotti
CONSTRUCTION AND BUILDING MATERIALS
(2020)
Article
Chemistry, Organic
Carolina S. Garcia, Paula M. Uberman, Sandra E. Martin
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Review
Chemistry, Organic
Maria E. Buden, Javier I. Bardagi, Roberto A. Rossi
CURRENT ORGANIC SYNTHESIS
(2017)
Article
Chemistry, Multidisciplinary
Liliana B. Jimenez, Marcelo Puiatti, Diego M. Andrada, Federico Brigante, Karina F. Crespo Andrada, Roberto A. Rossi, Ronny Priefer, Adriana B. Pierini