Article
Chemistry, Organic
Sensheng Liu, Yangbin Liu, Arthur Flaget, Cheng Zhang, Clement Mazet
Summary: This study describes a Cu-catalyzed regio- and enantioselective protoboration of 2,3-disubstituted 1,3-dienes. The protocol operates under mild conditions and is applicable to symmetrically and unsymmetrically substituted dienes, providing access to homoallylic boronates with consistently high yield, regioselectivity, and enantiomeric ratio. Preliminary investigations suggest a complex mechanism.
Article
Chemistry, Organic
Ze-Ran Jing, Dong-Dong Liang, Jin-Miao Tian, Fu-Min Zhang, Yong-Qang Tu
Summary: A new and efficient method for the preparation of 2-aryl-2,3-dihydrobenzofuran scaffolds with excellent enantioselectivities and high yields has been developed through the Cu/SPDO-catalyzed [3 + 2] cycloaddition between quinone ester and styrene derivatives. Moreover, the asymmetric synthesis of natural corsifurans A and B from commercially available starting materials has been accomplished in two or three steps using this reaction as a key transformation.
Article
Chemistry, Organic
Hyojin Cha, Jin Young Chai, Hyeong Baik Kim, Dae Yoon Chi
Summary: This study successfully synthesized fourteen aliphatic alpha-ketoamides through metal-catalyzed aerobic oxidative amidations, providing a strategy for improving the synthesis of aryl alpha-ketoamides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Fang Xie, Shijie Dong, Yajun Sun, Wenxing Liu, Xiaodan Liu, Lu Liu, Qin Zhao, Jiangli Wang
Summary: A CuH-catalyzed coupling reaction between aryl alkenes and 3-aryl-2H-azirines has been developed to synthesize optically active beta,beta-disubstituted ketones. The reaction proceeds via the regioselective attack of a chiral alkylcopper complex on the N-C2 bonds of azirines, generating chiral beta-aryl imines that can be further hydrolyzed to give ketones. This method provides a novel and efficient approach for the synthesis of chiral beta,beta-disubstituted ketones under mild conditions.
Article
Chemistry, Organic
Yu Sun, Jiayu Pan, Xiuqi Wang, Xiaoli Bu, Mengtao Ma, Fei Xue
Summary: A rhodium-catalyzed tandem arylation/cyclization reaction of 3-(ortho-boronated aryl) conjugated enones with unactivated alkynes is described. The use of a rhodium(I)/chiral-diene complex as the catalyst afforded various 2,3-disubstituted indene compounds with high yields, excellent regioselectivities, and enantioselectivities. This approach is attractive as it utilizes simple starting materials such as diarylalkynes, dialkylalkynes, and alkyl(aryl)alkynes.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Hyung Yoon, Alexandra Galls, Soren D. Rozema, Scott J. Miller
Summary: Enantioselective Cu-catalyzed C-O cross coupling reactions have been developed to yield atropisomeric resorcinol-bearing quinazolinones. By using a new guanidinylated dimeric peptidic ligand, the desired products were obtained with good yields and excellent stereocontrol. The reaction was easily scalable and various product derivatizations were carried out.
Article
Chemistry, Multidisciplinary
Raed M. Al-Zoubi, Walid K. Al-Jammal, Mazhar S. Al-Zoubi, Robert McDonald, Ahmad Zarour, Aksam Yassin, Abdulla Al-Ansari
Summary: An efficient and highly selective method for synthesizing 2,3-diiodinated N-aryl carbamate derivatives has been described in this study, with high yields and applicability to various functional groups.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Xuan Wu, Weiping Wu, Shuaixin Fan, Xuanzhen Han, Zhixin Wang, Hanxiao Xu, Baochen Wang, Jin Zhu
Summary: Multi-heteroatom heterocycle synthesis through direct C-H bond activation is challenging yet appealing. In this study, a double C-N bond formation sequence to prepare quinazolinones was achieved using primary amides and oxadiazolones in a catalytic redox-neutral system. The amide-directed C-H bond activation and oxadiazolone decarboxylation played vital roles in the efficient and atom-economic construction of the quinazolinone skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiaofeng Jie, Yingying Zhao, Qinglei Chong, Fanke Meng
Summary: A catalytic chemo- and enantioselective method for generating secondary benzylic copper complexes from Cu-B(pin) additions to 1,2-disubstituted aryl alkenes, followed by site-selective cyanation at either aryl group or benzylic position, is presented. The study identifies chiral Cu complexes that offer not only high enantioselectivity but also superior efficiency compared to achiral catalysts. This method also reveals an unprecedented mode of cyanation at the benzylic site through dearomative isomerization. The functionalization of the resulting alkylboron products provides valuable building blocks that are otherwise difficult to access.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Aaron F. Baldwin, Michaella A. Caporello, Guoyong Chen, Adam E. Goetz, Weifeng Hu, Chengfeng Jin, Kevin M. Knopf, Zhifeng Li, Cuong Lu, Sebastien Monfette, Angela L. A. Puchlopek-Dermenci, Feng Shi
Summary: The study presents a scalable method for preparing aminopyrazole building blocks using copper-catalyzed amidation. This alternative approach avoids the standard nitration/reduction sequence and associated risks.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Organic
Shaodong Kang, Jiaxing Li, Qin Yang, Zhibin Song, Yiyuan Peng
Summary: An efficient method for accessing 2-(2-beta-aryl ketone) substituted 2-arylquinazolinones has been described. 2-Carboxyl allylic alcohols derived from Morita-Baylis-Hillman adducts were used as the building blocks. The reaction between 2-aryl quinazolinones and 3-hydroxy-2-methylene-5-phenylpentanoic acid, catalyzed by [RhCp*Cl-2](2)-CF3COOAg, underwent C-H activation and decarboxylation to provide the desired products in good to excellent yields. Control experiments suggested that the nitrogen atom at the 3-position of the quinazolinone scaffold might serve as the directing group in this C-H activation/functionalization. A plausible mechanistic pathway for the synthesis of the target compounds is proposed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Seoung-Tae Kim, Michael J. Strauss, Albert Cabre, Stephen L. Buchwald
Summary: A new class of anionic ligands for Cu-catalyzed C-N couplings has been developed, which enables efficient amination of aryl bromides under mild conditions. This ligand design increases the electron density on Cu and stabilizes the active anionic CuI complex, leading to enhanced reactivity and a broad substrate scope.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Tzu-Lun Liu, Meng-Li Jhou, Cheng-En Hsieh, Chia-Jung Lin, Hsiu-Hui Su, Chih-Ming Chou
Summary: This study presents a protocol for the preparation of functionalized N-allyl-N-aryl sulfonamides via palladium-catalyzed intramolecular decarboxylative N-allylation reaction, showing good regioselectivity. Additionally, transformation of N-allyl-N-aryl sulfonamide into 4-aryl-1,2,3,4-tetrahydroquinoline and nitrogen-containing beta-hydroxysulfide bioactives has been demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Wei-Yang Ma, Coralie Gelis, Damien Bouchet, Pascal Retailleau, Xavier Moreau, Luc Neuville, Geraldine Masson
Summary: A highly enantio- and regioselective (3 + 2) formal cycloaddition catalyzed by a BINOL- and SPINOL-derived phosphoric acid is reported, leading to the synthesis of a wide variety of 2,3-disubstituted 2-aminoindolines with generally high yields and excellent enantioselectivities. The reaction showed moderate to complete diastereoselectivities in most cases, producing products with up to 98% yield and up to 99% ee.
Article
Chemistry, Applied
Ying Fu, Liang-Liang Guo, Xi Chen, Hao Chen, Jia-Jia Liu, Fang-Rong Li, Cai-Qin Xiao, Zhengyin Du
Summary: A Cu/Pd co-catalyzed Catellani-type ortho arylation reaction of iodoarenes with aryl diazonium salts has been developed. Aryl radicals that derived from aryl diazonium salts were regioselectively installed at ortho position of iodoarenes via palladium catalyzed C-H activation. Mechanistic studies showed that, in contrast to classical Pd0-PdII-PdIV-PdII-Pd0 catalytic cycle, this radical cascades performed via a Pd0-PdII-PdIII-PdI-Pd0 cycle.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
