Article
Chemistry, Organic
Yinpeng Wang, Mingming Zhao, Jingke Peng, Hongxia Zheng, Heng-Ying Xiong, Guangwu Zhang
Summary: The first Pd(0)-catalyzed synthesis of aryl-methylene ethers from hydrobenzoxazoles (hydrothiazoles) using dichloromethane (DCM) as the C1 feedstock is reported. This protocol demonstrates a broad substrate scope (38 examples) and wide tolerance to functional groups. The aryl-methylene ether adducts have been successfully coupled with isocyanate to provide bis-iminoisoindolinones. In this reaction, DCM serves as a twofold electrophile, undergoing double C-Cl bond cleavage to react with hydrobenzoxazoles.
Article
Chemistry, Organic
Tao Liu, Lingli Han, Jing Zhang, Gang Lu
Summary: Density functional theory calculations were used to investigate the competing pathways of rhodacycle intermediates in Rh(III)-catalyzed annulations of 2-alkenyl phenols and 2-alkenyl anilides with alkynes. The results reveal that the multiple pathways of eight-membered rhodacycles can be subtly tuned to give specific cyclic products. The formation of different cyclic products from 2-alkenyl phenols and 2-alkenyl anilides is governed by different pathways involving the dissociation of Rh-O bond and intramolecular olefin migratory insertion, respectively.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Hidenori Matsuyama, Xuan Zhang, Masahiro Terada, Tienan Jin
Summary: A versatile method for synthesizing alkylidene fluorenes and their heteroarene derivatives has been successfully developed by using a Pd(II)-catalyzed direct C-H/C-H coupling of o-alkenyl biaryls. Under aerobic oxidation conditions, the use of Pd(OAc)2 catalyst produces alkylidene fluorenes with various functional groups and diverse polycyclic systems. These resulting products can be utilized as versatile synthetic building blocks for constructing structurally diverse polycyclic arenes and heteroarenes.
Article
Chemistry, Multidisciplinary
Yulei Wang, Joao C. A. Oliveira, Zhipeng Lin, Lutz Ackermann
Summary: The study introduces the first electrochemical metal-catalyzed [5+2] cycloadditions, assembling seven-membered benzoxepine skeletons with a high substrate scope and efficiency. The mechanistic studies support a rhodium(III/I) regime involving a benzoxepine-coordinated rhodium(I) sandwich complex as the catalyst resting state.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Inorganic & Nuclear
Reike Clauss, Saral Baweja, Dmitri Gelman, Evamarie Hey-Hawkins
Summary: A series of novel heterobimetallic Pd-II/M-II complexes were synthesized and exhibited a cooperative effect in catalyzing coupling reactions, leading to improved catalytic activity and selectivity for the formation of various Z-alkenes. The homogeneous nature of the catalytically active species was also demonstrated in the study.
DALTON TRANSACTIONS
(2022)
Review
Chemistry, Applied
Xi Sun, Xu Dong, Hui Liu, Yuying Liu
Summary: Great improvements have been made in palladium-catalyzed radical reactions in recent years, offering more effective strategies for constructing complex heterocyclic compounds and applications in drug discovery. Reactions mediated by Pd(0)/(II)/(IV) typically undergo two-electron transfer processes, while those involving Pd(I) and Pd(III) usually occur via single electron transfer processes. Numerous methodologies involving palladium radical have emerged in the past five years since the publication of the review.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Yang Liu, Mikael La Roch, Alessia Mori, Alexandre Pradal, Giovanni Poli, Julie Oble
Summary: The article introduces a Pd(II)-catalyzed [3+2] annulation strategy, which replaces α,β-unsaturated-γ-oxy carbonyls with β,γ-unsaturated carbonyl derivatives as bis-electrophiles. The study provides experimental optimization and demonstrates the synthetic versatility in forming diverse heterocyclic structures. This dehydrogenative strategy represents a more economical version than the previous redox-neutral couplings.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Takashi Mino, Yohei Fujisawa, Shizuki Yoshida, Mitsuru Hirama, Takumu Akiyama, Ryo Saito, Yasushi Yoshida, Yoshio Kasashima, Masami Sakamoto
Summary: By synthesizing cinnamoyl amide type chiral P,olefin ligand (S)-4, separable diastereomers of 4d were obtained successfully, and asymmetric allylic substitution reactions of indoles using (S,aS)-4d as a chiral ligand demonstrated high enantioselectivities (up to 98% ee).
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Zhuo-Zhuo Zhang, Gang Zhou, Fan-Rui Huang, Bing-Feng Shi
Summary: A cobalt-catalyzed method was developed for the expedited synthesis of tetrahydrofuro[2,3-c]isoquinolinones from benz-amides and dihydrofuran, using commercially available and inexpensive Co(OAc)(2)center dot 4H(2)O as an efficient catalyst. Various functional groups were tolerated, leading to the desired products with high yields, excellent regioselectivity, and good diastereoselectivity under mild conditions.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Yan Li, Lina Geng, Zhiyi Song, Zhiqiang Zhang
Summary: In this study, the mechanisms and regio- and stereoselectivities of NHC-catalyzed reactions of 2-bromoenals with thioamides leading to the formation of 1,3-thiazin-4-ones were investigated using density functional theory. The study found that the thia-Michael addition step is the determining factor for the regio- and stereoselectivity, with the S-configurational product being preferentially formed.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiang Wu, Li-Ping Zhao, Jin-Ming Xie, Yan-Ming Fu, Cheng-Feng Zhu, You-Gui Li
Summary: This study describes a gold-catalyzed cyclization reaction for the synthesis of 3-sulfonamidoquinolines, featuring a rare and highly selective 1,2-N migration. The key alpha-imino gold carbene intermediate is generated through an intramolecular nucleophilic attack of the azide group to the Au-activated triple bonds in a 6-endo-dig manner.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xiang Wu, Li-Ping Zhao, Jin-Ming Xie, Yan-Ming Fu, Cheng-Feng Zhu, You-Gui Li
Summary: A gold-catalyzed cyclization for the synthesis of 3-sulfonamidoquinolines is described, featuring a rare and highly selective 1,2-N migration of the key alpha-imino gold carbene intermediate.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Floriane Doche, Julien Escudero, Fabien Petit-Cancelier, Heng-Ying Xiong, Samuel Couve-Bonnaire, Davide Audisio, Thomas Poisson, Tatiana Besset
Summary: This study investigated the unprecedented Pd-catalyzed (ethoxycarbonyl)difluoromethylthiolation reaction and successfully functionalized unsaturated derivatives under mild reaction conditions, providing a new method for synthesis.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Review
Chemistry, Multidisciplinary
Naish Lalloo, Conor E. Brigham, Melanie S. Sanford
Summary: Transition-metal-catalyzed decarbonylative coupling reactions using carboxylic acid derivatives as electrophiles have the advantages of abundant and inexpensive reactants. This Account highlights the development of base-free decarbonylative coupling reactions catalyzed by group 10 metals and discusses the catalyst design guided by stoichiometric organometallic studies. The article also discusses the challenges and future directions in this field.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Biochemistry & Molecular Biology
Ida Ziccarelli, Lucia Veltri, Tommaso Prestia, Roberta Amuso, Maria A. Chiacchio, Raffaella Mancuso, Bartolo Gabriele
Summary: Unreported 2-(4-acylfuran-2-yl)acetamides were selectively synthesized in fair to good yields (54-81%) over 19 examples through a mild catalytic process involving Csp-H activation, 5-exo-dig O-cyclization, and aromative isomerization.
Article
Chemistry, Multidisciplinary
Woon-Yew Siau, Wenjun Li, Fei Xue, Qiao Ren, Minghu Wu, Shaofa Sun, Haibing Guo, Xuefeng Jiang, Jian Wang
CHEMISTRY-A EUROPEAN JOURNAL
(2012)
Article
Chemistry, Physical
Zhihui Ai, Lirong Lu, Jinpo Li, Lizhi Zhang, Jianrong Qiu, Minghu Wu
JOURNAL OF PHYSICAL CHEMISTRY C
(2007)
Article
Materials Science, Multidisciplinary
WD Zou, ZL Liu, MH Wu, KL Yao
JOURNAL OF MAGNETISM AND MAGNETIC MATERIALS
(2005)
Article
Physics, Condensed Matter
WD Zou, ZL Liu, MH Wu, KL Yao
PHYSICA B-CONDENSED MATTER
(2004)
Article
Chemistry, Organic
MH Wu
SYNTHETIC COMMUNICATIONS
(2000)
