Article
Chemistry, Organic
Yi-Xin Xu, Yu-Qing Liang, Zhong-Jian Cai, Shun-Jun Ji
Summary: A novel chelation-assisted C-H arylation reaction of benzo[h]quinoline is described in this study. The reaction, using [RuCl2(p-cymene)]2 as the catalyst and cheap and easily accessible arylsulfonyl chlorides as the arylation source, exhibits simple reaction conditions, a broad substrate scope, and good functional group tolerance. The successful application of bioactive-molecule-based sulfonyl chlorides further emphasizes the potential utility and importance of this desulfitative C-H arylation protocol.
Article
Chemistry, Organic
Haotian Sun, Baojian Xiong, Yuan Yang, Jiangjun Liu, Xuemei Zhang, Zhong Lian
Summary: A novel dual nickel/palladium-catalyzed reaction has been developed for the synthesis of compounds containing gem-difluorovinyl fragments, showing excellent stereoselectivity and yields. The method also exhibits good functional group tolerance.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Ikuya Fujii, Kazuhiko Semba, Yoshiaki Nakao
Summary: Rhodium-aluminum bimetallic complexes catalyze the Kumada-Tamao-Corriu (KTC) cross-coupling reaction using arylmagnesium compounds generated from corresponding aryl fluorides or chlorides. This method allows the challenging KTC coupling reaction to be carried out using aryl fluorides as nucleophiles, resulting in various biaryls.
Article
Chemistry, Organic
Kodai Yamada, Mika B. Kintzel, Gregory J. P. Perry, Hayate Saito, Hideki Yorimitsu
Summary: The formation of zinc reagents by the reaction of styrylsulfonium salts with zinc powder is reported, without the need for transition metals or other additives. The method shows good tolerance towards a variety of sensitive functional groups and can be used in various functionalizations.
Article
Chemistry, Applied
Pengbo Zhang, Wenwu Li, Xianglong Zhu, Ying Li, Xiangmei Zhao, Saige Shi, Fengxiang Zhu, Jinming Lin, Xia Gao
Summary: A photoredox and copper-catalyzed sulfonylphosphorothiolation of alkenes has been developed, allowing the synthesis of a wide range of decorated beta-sulfonyl phosphorothioates. The reaction shows good functional group tolerance and can be conveniently used for late-stage modification of bioactive molecules and gram-scale synthesis.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Yanting Yu, Zhigang Wang, Zeguo Fang, Qian Zhang, Dong Li
Summary: A novel method for synthesizing beta-hydroxylsulfone derivatives by cobalt-catalyzed aerobic oxysulfonylation of styrenes with sulfonyl chlorides was developed. This reaction occurs under simple and mild conditions, using inexpensive cobalt as the catalyst and molecular oxygen as the oxidant. It demonstrates a broad substrate scope and provides a series of beta-hydroxylsulfones in moderate to good yields.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xuan-Di Song, Meng-Meng Guo, Shuang Xu, Chuanji Shen, Xiaocong Zhou, Xue-Qiang Chu, Mengtao Ma, Zhi-Liang Shen
Summary: A nickel-catalyzed direct reductive cross-coupling of disubstituted cycloalkyl iodides with aryl iodides was developed, allowing for efficient stereocontrolled synthesis of a variety of cross-coupled products with high diastereoselectivity and wide functional group tolerance. The one-pot reaction is simple to operate, providing a convenient method for the synthesis of complex molecules.
Article
Chemistry, Organic
David J. Charboneau, Nilay Hazari, Haotian Huang, Mycah R. Uehling, Susan L. Zultanski
Summary: This article summarizes the recent progress in the use of homogeneous organic electron donors in Ni-catalyzed cross-electrophile coupling reactions and discusses their advantages and limitations in synthetic chemistry. The discussion of the strengths and weaknesses of different methods for introducing electrons is also applicable to other reductive transformations.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Bingbing Dong, Jiansha Lu, Honghao Bao, Yuanyuan Zhang, Yingguo Liu, Yuting Leng
Summary: This copper-catalyzed reaction allows for the radical cross-coupling of cyclobutanone oxime esters with sulfonyl hydrazides, producing a wide range of diversely substituted cyano-containing sulfones. The method is notable for its low-cost catalytic system, lack of toxic reagents, and use of readily accessible starting materials.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Dmitrii Kalinin, Trond Ulven
Summary: A chemoselective Pd-mediated carbonylative Negishi-type catalytic protocol for the synthesis of (hetero)-aryl ketones is described. The protocol utilizes the PEPPSI-IPr precatalyst and CO gas at atmospheric pressure to facilitate the carbonylative coupling between various C-(sp3)-hybridized organozinc reagents and a wide range of aryl iodides, including substrates with aldehyde, aniline, phenol, or carboxylic acid groups, and heteroaryls.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Li-Ming Zhang, Wenjun Luo, Jiangzhen Fu, Yu Liu, Junliang Zhang
Summary: A newly developed PNP-type W-Phos ligand showed a unique effect on the catalytic asymmetric addition of reactive Grignard reagents to ketimines. This enabled a Cu(I)-catalyzed asymmetric alkylation reaction of N-sulfonyl ketimines, resulting in the formation of optically active α-tertiary amines with high enantioselectivities.
Letter
Chemistry, Organic
Na-Na Ma, Xuan-Bo Hu, Yuan-Shuai Wu, Ya-Wen Zheng, Mengtao Ma, Xue-Qiang Chu, Hao Xu, Haiqing Luo, Zhi-Liang Shen
Summary: A direct cross-coupling reaction of aryl thioether with aryl bromide was successfully achieved using nickel salt, magnesium, and lithium chloride as catalysts in tetrahydrofuran solvent at room temperature. The one-pot reactions efficiently cleaved the C-S bond, yielding the desired biaryls in moderate to good yields, without the need for pregenerated or commercial organometallic reagents.
Article
Chemistry, Organic
Xuejing Peng, Jingxian Huang, Guan-Yu Han, Xing-Zhong Shu
Summary: In this manuscript, a dynamic kinetic cross-electrophile coupling reaction of benzylic alcohols with alkenyl triflates is reported. This method allows for the replacement of the alcohol group with an alkenyl functionality, resulting in versatile benzyl-substituted cyclic alkenes. The reaction is orthogonal to existing reductive coupling methodologies and tolerates various functional groups.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Wen-Xin Li, Bo-Wen Yang, Xuan Ying, Zhuo-Wen Zhang, Xue-Qiang Chu, Xiaocong Zhou, Mengtao Ma, Zhi-Liang Shen
Summary: The direct cross-coupling of diaryl sulfoxides with aryl bromides via C-S bond cleavage was achieved using nickel(II) as the catalyst, 1,2-bis(diphenylphosphino)ethane (dppe) as the ligand, and magnesium turnings as the reducing metal in THF. This reaction showed a wide range of substrates and could be used for gram-scale synthesis. The one-pot reaction is operationally simple and economically efficient.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Wangsheng Liu, Lin Hao, Junmin Zhang, Tingshun Zhu
Summary: Electrosynthesis has gained more attention recently for its potential in replacing chemical oxidants or reductants in molecule-electrode electron transfer. Sulfonyl compounds have been found as practical precursors of several radicals, and electrochemical redox reactions offer green and efficient pathways for activating these compounds.
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)