Article
Chemistry, Organic
Gurupada Hazra, Gitanjali Mishra, Rambabu Dandela, Barla Thirupathi
Summary: The dibenzobicyclo[3.2.1]octadienone scaffold, found in various compounds such as naphthocyclinones, engelharquinones, and rubialatin A, has been successfully synthesized using a mild transition metal-free aryne insertion reaction. The methodology has been applied to the synthesis of the 6/6/5/6/6 scaffold of rubialatin A. H-1 NMR experimental studies confirm the reaction mechanism involves the formation of a benzocyclobutane followed by a 7-member carbocycle ring.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xiang Liu, Xiaotian Shi, Jinlei Zhou, Changfeng Huang, Yu Lin, Chen Zhang, Hua Cao
Summary: Dearomatization reactions provide a rapid and efficient method for constructing complex molecules, such as densely functionalized indolizinones, from simple aromatic compounds. The authors developed a metal-free dearomative cycloaddition reaction and a cyclization reaction, which are highly effective in synthesizing a variety of benzo-fused indolizinones. Density functional theory calculations revealed the critical role of an appropriate substituent at the 2-position of pyridine in the dearomatization process.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Rong-Bin Hu, Shengsheng Qiang, Yung-Yin Chan, Jingxian Huang, Tianyue Xu, Ying-Yeung Yeung
Summary: A catalytic synthesis of halogenated gamma-butenolides from cyclopropene carboxylic acids was developed using zwitterionic catalysts and N-haloamides as the halogen sources in this study. The catalytic protocol could also be applied to the synthesis of halogenated pyrrolones using cyclopropene amides as the starting materials.
Article
Chemistry, Organic
Kangdong Mo, Xiaocong Zhou, Ju Wu, Yufen Zhao
Summary: A robust and green electrochemical method was developed for the dearomatization of indoles, where a fluorine-containing group was merged with an indole nucleus under oxidant-free conditions, resulting in the synthesis of a diverse array of tri- and difluoromethylated 3,3-spiroindolines with good functional group tolerance.
Article
Chemistry, Organic
Hui-Qi Yue, Qi-Wei Li, Da-Wei Shi, Rui-Jia Yang, Liang-Liang Han, Bin Yang
Summary: Herein, we disclose a novel PPh3-mediated nucleophilic sulfonation method of sulfonyl chlorides with arynes, providing a direct approach to various aryl and alkyl sulfones. The protocol exhibits broad functional group tolerance and the valence state of the sulfur atom remains unchanged.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Matteo Lanzi, Racha Abed Ali Abdine, Maxime De Abreu, Joanna Wencel-Delord
Summary: This study reported the synthesis of dissymetric 2,3,2',3',4-substituted biaryls via pericyclic reactions of cyclic diaryl lambda(3)-bromanes. The method provides functional group tolerance and atom economy, allowing access to molecular complexity in a single reaction step. Continuous flow protocol has been designed for scale-up, while postfunctionalizations have been developed leveraging the residual Br-atom.
Article
Chemistry, Organic
Kangdong Mo, Xiaocong Zhou, Ju Wu, Yufen Zhao
Summary: An efficient and environmentally friendly electro-chemical method has been developed for the dearomatization of indoles. This method yielded a series of azido-containing spirocyclic indolines with good tolerance to functional groups. Cyclic voltammetry experiments supported the proposed mechanism involving the oxidation of Mn-II-N-3 species. Synthetic transformations offer an alternative approach for the synthesis of functionalized indolines.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Kailas V. Preeti, Kailas V. Kallurkar, Prathama S. Mainkar, Raju Adepu, Srivari Chandrasekhar
Summary: A concise route for the synthesis of dihydrobenzo-[j]-phenanthridinones has been developed using an aryne annulation strategy under metal-free reaction conditions. The reaction involves multiple C-C and C-N bond cleavages/formations through Diels-Alder reaction, aromatization-driven C-N bond cleavage, and amide formation.
Article
Chemistry, Physical
Geng-Xin Liu, Xiao-Ting Jie, Xing-lin Li, Li-Sheng Yang, Huang Qiu, Wen-Hao Hu
Summary: We have designed and developed a general strategy for synthesizing multisubstituted 1,3-diene derivatives. This method involves the cleavage of cyclopropenes via rearrangement of the cyclopropyl radical to the allyl radical, followed by the addition of a carbon-centered radical with a leaving group onto the strained double bond. The resulting 1,3-diene products are highly valuable and exhibit good antitumor activity.
Article
Chemistry, Physical
Amit Kumar Simlandy, Mao-Yun Lyu, M. Kevin Brown
Summary: The paper presents a method for synthesizing highly substituted spirocyclic cyclobutanes through catalytic arylation of cyclobutenes using Cu/Pd or Ni catalysts. The identification of a suitable Cu complex for arylboration is crucial for achieving high selectivity in Cu/Pd catalyzed reactions. The synthetic utility of the products is demonstrated, with mechanistic details discussed.
Article
Chemistry, Multidisciplinary
Anil Kumar, Kandikere Ramaiah Prabhu
Summary: A new [5+1] annulation reaction has been discovered, leading to the efficient synthesis of valuable compounds with unique chemical structures in a single step. The process demonstrates broad substrate scope and good functional group tolerance.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Applied
Sergio Fernandez, Dario Allegue, Javier Santamaria, Alfredo Ballesteros
Summary: A gold-catalyzed bispropargylation reaction of xanthone derivatives is described. The use of propargylsilanes allows for a deoxygenative bispropargylation through the catalytic addition of the allenylgold intermediate to the activated carbonyl moiety. This reaction shows diastereoselectivity with both xanthone and thioxanthone derivatives.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Shan Liu, An-Jing Wang, Min Li, Jing Zhang, Guo-Dong Yin, Wen-Ming Shu, Wei-Chu Yu
Summary: A tandem reaction for the synthesis of (quinazolin-2-yl)methanone derivatives has been explored using Rh(III) catalysis, involving denitrogenation of alpha-azido ketones, aza-[4 + 2] cycloaddition with 2,1-benzisoxazoles, ring opening, and dehydration aromatization processes.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Shan Liu, An-Jing Wang, Min Li, Jing Zhang, Guo-Dong Yin, Wen-Ming Shu, Wei-Chu Yu
Summary: A Rh(III)-catalyzed tandem reaction has been developed for the synthesis of (quinazolin-2-yl)methanone derivatives from 2,1-benzisoxazoles and alpha-azido ketones, involving denitrogenation, aza-[4 + 2] cycloaddition, ring opening, and dehydration aromatization processes, with the aza-[4 + 2] cycloaddition being the key step.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Sumit Das, Shantonu Roy, Arup Bhowmik, Writhabrata Sarkar, Imtiaj Mondal, Aniket Mishra, Shubhra Jyoti Saha, Sudip Karmakar, Indubhusan Deb
Summary: This study establishes a straightforward strategy for the direct incorporation of sulfonyl units into a xanthene moiety, yielding xanthen-9-sulfone derivatives in good to excellent yields via metal-free radical-radical cross-coupling reaction. The methodology uses easily accessible starting materials and proceeds efficiently under simple reaction conditions with a high degree of functional group compatibility.
CHEMICAL COMMUNICATIONS
(2022)
