Review
Biochemistry & Molecular Biology
Ramsha Munir, Ameer Fawad Zahoor, Sadia Javed, Bushra Parveen, Asim Mansha, Ahmad Irfan, Samreen Gul Khan, Ali Irfan, Katarzyna Kotwica-Mojzych, Mariusz Mojzych
Summary: Simmons-Smith cyclopropanation is a widely used reaction in organic synthesis for the conversion of alkenes into cyclopropane. It is an important reaction because cyclopropane is a key intermediate in the synthesis of biologically active natural compounds. The modified form of this reaction using Et2Zn and CH2I2 has been successfully applied in the total synthesis of complex natural products with diverse biological activities. This review provides an overview of the Furukawa-modified Simmons-Smith cyclopropanation from 2005 to 2022.
Article
Chemistry, Applied
Jose Luis Nova-Fernandez, Gustavo Pascual-Coca, Silvia Cabrera, Jose Aleman
Summary: Flow chemistry has opened new chemistry windows by enabling the safer use of hazardous and sensitive reagents. It outperforms batch counterparts due to improved mass and heat transfer, offering great potential for industrial application.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Engineering, Chemical
Yakun Liu, Shennan Yang, Chengxiang Shi, Lun Pan, Xiangwen Zhang, Jin-Jun Zou
Summary: A highly active solid acid catalyst for the cyclopropanation of dicyclopentadiene has been prepared by impregnation method. The catalyst shows good catalytic activity and recyclability, providing a green and efficient synthesis for high-energy-density fuel, pesticide and medicine.
CHEMICAL ENGINEERING SCIENCE
(2024)
Article
Multidisciplinary Sciences
Shaoze Yu, Hanyang Bao, Dekun Zhang, Xiaoyu Yang
Summary: This work reports an efficient and versatile kinetic resolution protocol for various substituted amido[2.2]paracyclophanes using chiral phosphoric acid (CPA)-catalyzed asymmetric amination reaction. The reaction mechanism for the electrophilic aromatic C-H amination is also elucidated, involving sequential triazane formation and N[1,5]-rearrangement.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Abhijit Manna, Harshit Joshi, Vinod K. Singh
Summary: A novel organocatalytic cascade approach has been developed for the synthesis of spiro-cyclopropyl oxindole derivatives. This methodology demonstrates remarkable stereocontrol, wide substrate scope, and scalability, and represents the first example of vinylogous Michael initiated ring closure reaction for the synthesis of chiral 3,3'-cyclopropyl oxindole.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Lorenzo Pontini, Jamie A. Leitch, Duncan L. Browne
Summary: This study presents a solvent-free method for synthesizing cyclopropanes via a ball-milling-enabled Simmons-Smith reaction. By utilizing mechanochemical techniques to activate zinc(0), this protocol, which is simple to operate under air, enables the synthesis of various cyclopropane structures and gram-scale production.
Article
Chemistry, Organic
Rui-Ying Zhang, Feng Jin, Xiao-Guang Bao, Hai-Yan Li, Xiao-Ping Xu, Shun-Jun Ji
Summary: A cascade reaction mediated by N-bromosuccinimide involving the cyclization/oxygen-migration/ring-contraction process of 3-(beta, beta-diaryl) indolylethanol was disclosed, leading to efficient synthesis of a variety of spiro 3,3'-cyclopropyl oxindole derivatives under mild reaction conditions. A possible mechanism was suggested based on intermediate isolation and computational studies.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Tong Hong, Yongchun Liu, Kun Zhao, Song Cheng, Qingsong Liu, Shuting Zhang, Ying Zhong, Xiaoxiao Li, Zhigang Zhao
Summary: A facile protocol for the synthesis of cyclopropyl groups through gold-catalyzed [2 + 1] cycloaddition is reported. The reaction exhibited good functional group tolerance and high efficiency, affording the products in good to excellent yields. Furthermore, the aldehyde can be converted to amide under Schmidt reaction conditions and alcohol under reduction conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Thirupathi Reddy Penjarla, Adarash Kumar Shukla, Rituparna Hazra, Durba Roy, Maheshwar Kundarapu, Mudit Dixit, Anupam Bhattacharya
Summary: This article reports the synthesis of spiro compounds based on an indanedione-cyclopropane-pyrazolone framework. The reaction was carried out using the Michael-initiated ring closure strategy under Cu(OAc)(2) catalysis, assisted by an oxygen atmosphere and the base Et3N. The obtained compounds were mostly inseparable mixtures with modest to good yields using diverse substrates. Computational studies suggested that a route involving a four-membered Cu containing intermediate is feasible. The developed method has the potential to synthesize other analogous spiro systems.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Min Ye, Fan Xu, Yun Bai, Fanglian Zhang, Wenjia Wang, Yiping Qian, Zhengwang Chen
Summary: A convenient and efficient annulation reaction method has been developed for the synthesis of dinitrile-substituted cyclopropanes. The method exhibits broad substrate compatibility and high yields, achieved through tandem Michael-type addition and intramolecular cyclization.
Article
Chemistry, Multidisciplinary
Hang Han, Bingbin Zhu, Xiaofan Du, Yu Zhu, Chuanming Yu, Xinpeng Jiang
Summary: A novel reaction for the synthesis of 1-azido-3-heteroaryl bicyclo[1.1.1]pentanes via azidoheteroarylation of [1.1.1]propellane is reported. This strategy allows for the direct installation of an azido group, providing an efficient route for synthetic organic chemistry applications.
Article
Chemistry, Organic
D. Basavaraja, C. S. Athira, V. Siddalingeshwar, K. T. Ashitha, Sasidhar B. Somappa
Summary: This article describes an efficient, straightforward, and one-pot synthesis method for biologically active spiro-dihydropyridine oxindoles. The method has great flexibility and yields good results, and the resulting products can be further modified into new compounds of pharmaceutical relevance.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yuya Kawai, Juntaro Nogami, Yuki Nagashima, Ken Tanaka
Summary: This study reports the enantio- and/or diastereoselective synthesis of planar chiral polycyclic aromatic hydrocarbon (PAH)-based [2.2]cyclophanes via base-mediated intermolecular macrocyclization and Rh- or Ni-catalyzed intramolecular double [2 + 2 + 2] cycloadditions. DFT calculations reveal that the diastereoselectivity is kinetically determined by the second [2 + 2 + 2] cycloaddition. Single crystal X-ray diffraction analyses confirm the repulsion between the facing triphenylene or [5]helicene skeletons, leading to curved structures with bulged centers.
Article
Chemistry, Organic
Chong-Yang Shi, Ji-Jia Zhou, Pan Hong, Bo-Han Zhu, Feng-Lin Hong, Peng-Cheng Qian, Qing Sun, Xin Lu, Long-Wu Ye
Summary: An efficient gold-catalyzed cascade cyclization has been developed for the synthesis of tetracyclic gamma-lactams bearing one quaternary carbon center and one tertiary carbon center. The reaction involves alkyne oxidation, carbene-alkyne metathesis, and cyclopropanation, and exhibits moderate to good yields with excellent diastereoselectivities. The proposed mechanistic rationale is well supported by theoretical calculations.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Xiaoju Tan, Kun Zhao, Xuefang Zhong, Lan Yang, Yiming Dong, Tianmi Wang, Shengping Yu, Xiaoxiao Li, Zhigang Zhao
Summary: An efficient potassium persulfate-mediated radical addition of allenamides with diselenides was developed for the synthesis of 1,2-diselenide products. The reaction shows good tolerance towards a wide range of functional groups and delivers the products in good to excellent yields. Mechanistic investigations suggest that the reaction proceeds through a radical cascade involving a vinyl radical intermediate.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)