Article
Multidisciplinary Sciences
Guodong Fan, Qingyun Wang, Jun Xu, Pengcheng Zheng, Yonggui Robin Chi
Summary: The authors reported a new method for selective reactions, in which the high selectivity is achieved through the observed redox properties between unsymmetric enedials and carbene catalysts. This method enables efficient synthesis of furo[2,3-b]pyrroles derivatives widely found in natural products and pharmaceuticals.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Min Wu, Yi Wang, Jing Zhou, Ting Wang, Hui Gao, Zhi Zhou, Wei Yi
Summary: A variety of 2,3,5-trisubstituted furans were successfully synthesized through the Rh(III)-catalyzed vinylic C-H coupling of N-enoxyimides with propargyl alcohols or amines. The key to achieving the desired chemo-/regioselectivity was the -OH/-NHR moiety in the alkynes. Mechanistic studies and DFT calculations revealed a sequential reaction pathway involving C-H activation, regioselective alkyne insertion, O-N bond cleavage, hydrogen transfer, intramolecular nucleophilic addition, and aromatization, with a distinct Rh(V) carbene species as the active intermediate.
Article
Chemistry, Organic
Kirill A. Gomonov, Vasilii V. Pelipko
Summary: This microreview analyzes and summarizes data on methods of synthesis of monocyclic polysubstituted furan-3(4)-carboxylates published over the past 6 years.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2022)
Article
Chemistry, Organic
Min Wu, Yi Wang, Jing Zhou, Ting Wang, Hui Gao, Zhi Zhou, Wei Yi
Summary: A variety of 2,3,5-trisubstituted furans were synthesized through a Rh(III)-catalyzed vinylic C-H coupling reaction of N-enoxyimides with propargyl alcohols or amines. The success of this protocol relied on the presence of the -OH/-NHR moiety in the alkynes, which played a crucial role in achieving the desired chemo-/regioselectivity. Detailed experimental mechanistic studies and DFT calculations revealed a sequential reaction path involving C-H activation, regioselective alkyne insertion, simultaneous O-N bond cleavage and hydrogen transfer, intramolecular nucleophilic addition, and aromatization, with a distinctive Rh(V) carbene species as the active intermediate.
Article
Chemistry, Organic
Min Wu, Yi Wang, Jing Zhou, Ting Wang, Hui Gao, Zhi Zhou, Wei Yi
Summary: A variety of 2,3,5-trisubstituted furans were synthesized by using a rhodium catalyst. The reaction involved the vinylic C-H coupling of N-enoxyimides with propargyl alcohols or amines. Mechanistic studies revealed the sequential steps of C-H activation, regioselective alkyne insertion, O-N bond cleavage, hydrogen transfer, intramolecular nucleophilic addition, and aromatization, with a distinctive Rh(V) carbene species as the active intermediate.
Article
Chemistry, Multidisciplinary
Markus Staudt, Theis Solling, Lennart Bunch
Summary: An anion-accelerated 2 π-electrocyclic ring opening reaction of 6,6-dihalobicyclo[3.1.0]hexan-2-ones at low temperature has been reported, which yields meta-halophenols in good yields. Some of the phenols have unconventional substitution patterns and are reported for the first time. The methodology was also successfully applied in the total synthesis of the phenolic natural product caramboxin.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Sunhee Lee, Sunmi Kim, Seok Hyun Yoon, Anuradha Dagar, Ikyon Kim
Summary: The novel domino mode of assembly discovered in a one-pot three-component reaction under mild and eco-friendly conditions led to the synthesis of a new tricyclic skeleton, involving consecutive formation of multiple bonds and construction of two rings in a diastereoselective manner.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Crystallography
Nabyl Merbouh, Simon Cassegrain, Wen Zhou
Summary: The crystal structures of two unsubstituted arylnaphthalene lactones and one non-aromatic dihydro arylnaphthene lactone were reported in the study, showing only minor differences in geometrical parameters and the presence of both isomers in the same asymmetric unit cell in certain cases.
Article
Chemistry, Organic
Abdolali Alizadeh, Behnaz Farajpour, Mojtaba Khanpour
Summary: This method does not require a metal catalyst or expensive starting materials, and the products can be easily purified by filtration and ethanol washing. Advantages include readily available starting materials, green and mild conditions, synthetically useful yields, and operational simplicity.
Article
Chemistry, Multidisciplinary
Masoumeh Imani, Nader Noroozi Pesyan, Michael Aalinejad, Ertan Sahin
Summary: A novel method has been developed for the one-pot reaction of 4-hydroxycoumarin with various aldehydes and trimethylamine, resulting in the formation of dicumarols and quaternary dicumarol-triethylammonium salts in the presence of cyanogen bromide. Additionally, it was found that 4-hydroxybenzaldehyde selectively and effectively formed dihydro-4H-furo[3,2-c]chromene derivative under the same conditions.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Robert Eckl, Sebastian Fischer, Carina M. Sonnleitner, Daniel Schmidhuber, Julia Rehbein, Oliver Reiser
Summary: The developed method offers a stereoselective, scalable, and metal-free approach for the ring-expansion of monocyclopropanated pyrroles and furans, leading to highly functionalized tetrahydropyridine and dihydro-2H-pyran derivatives. This selective cleavage of unactivated endocyclic cyclopropane C-C bonds allows for targeted transformations of the resulting six-membered heterocycles, providing versatile building blocks with relevance for drug synthesis.
ACS ORGANIC & INORGANIC AU
(2021)
