Article
Chemistry, Organic
Hua Yao, Xiaoyang Zhong, Bingqing Wang, Sen Lin, Zhaohua Yan
Summary: A novel and efficient approach for the amine-directed dehydrogenative C(sp(2))-C(sp(3)) coupling of arylamines with acetonitrile was developed using FeCl2 as the catalyst. The method provides a straightforward and green route to arylacetonitriles with good regioselectivity and excellent compatibility of functional groups and aromatic rings.
Article
Chemistry, Multidisciplinary
Rongxiang Chen, Bing Liu, Wenbo Li, Kai-Kai Wang, Changqing Miao, Zhizhuang Li, Yingjie Lv, Lantao Liu
Summary: This methodology describes a PIDA-promoted cross-dehydrogenative coupling reaction between N-hydroxyphthalimide (NHPI) and aryl ketones for efficient synthesis of N-alkoxyphthalimide products in moderate to good yields, which is characterized by catalyst-free conditions, readily available starting materials, wide substrate scope, and operational simplicity. Additionally, a gram-scale reaction and synthetic transformation of the product into synthetically useful intermediates have been demonstrated.
Article
Chemistry, Organic
Huan Cao, Chao-Jiu Long, Dan Yang, Zhi Guan, Yan-Hong He
Summary: An unprecedented electrochemical cross-dehydrogenative coupling reaction has been developed for the direct synthesis of alpha-substituted isochromans. This method allows for the direct activation of C(sp3)-H bond adjacent to the O atom of isochroman. It has high atom economy, does not require a chemical oxidant, and is carried out under mild conditions using methanesulfonic acid as both electrolyte and catalyst, making it convenient and environmentally friendly. Gram-scale experiments and synthesis of antitumor active compounds demonstrate the practical applicability of this protocol.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Huan Cao, Chao-Ji u Long, Dan Yang, Zhi Guan, Yan-Hong He
Summary: An unprecedented electrochemical cross-dehydrogenative coupling reaction has been developed for the direct synthesis of α-substituted isochromans by coupling isochroman with unactivated ketones. This method allows for the direct activation of the C(sp(3))-H bond adjacent to the O atom of isochroman and features high atom economy, chemical oxidant-free conditions, and mild reaction conditions. Methanesulfonic acid (MsOH) serves as both electrolyte and catalyst, making the process more convenient and environmentally friendly. Gram-scale experiments and synthesis of antitumor active compounds demonstrate the practical potential of this protocol.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Chunhui Jiang, Xuefei Sha, Cheng Ni, Wei Qin, Xuejie Zhu, Shan Wang, Xuan Li, Hongfei Lu
Summary: A visible-light-induced dehydrogenative/decarboxylative coupling reaction of arylglycine derivatives and beta-keto acids is described, which allows for efficient synthesis of gamma-keto glycine derivatives under ambient conditions. This photocatalyst- and additive-free protocol also demonstrates further uses of this methodology and a plausible mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Le-Cheng Wang, Bo Chen, Xiao-Feng Wu
Summary: A novel cobalt-catalyzed carbonylative coupling of ethers with amines has been achieved, leading to the synthesis of biologically active compounds. This protocol presents the first example of direct carbonylative reaction of ethers, providing an important method for the construction of alpha-carbonylated ethers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Inorganic & Nuclear
Zhenwei Ni, Rosa Padilla, Rajib Pramanick, Mike S. B. Jorgensen, Martin Nielsen
Summary: A base-free, acceptorless dehydrogenative coupling of ethanol to ethyl acetate is achieved using a pincer complex ((PNP)-P-Ph)RuH(BH4)(CO) (0.25 mol%) and m-xylene as the co-solvent. The catalysis shows excellent conversion and yield of >99% after 24 h at 120 degrees C. The scaled-up reaction is also effective under similar conditions.
DALTON TRANSACTIONS
(2023)
Review
Chemistry, Multidisciplinary
Jianbin Li, Chia-Yu Huang, Chao-Jun Li
Summary: This review summarises recently developed strategies for achieving C-C cross-couplings between an inert aliphatic C-H bond and another C-H bond through different C(sp3)-H functionalisation tactics.
TRENDS IN CHEMISTRY
(2022)
Article
Chemistry, Applied
Heng Li, Jiajia Chen, Juncheng Zhang, Ping Liu, Peipei Sun
Summary: A direct amination of quinoxalin-2(1H)-ones via electrochemical C(sp(2))-H/N-H cross dehydrogenative coupling has been achieved using TMSN3 as the hydrogen atom transfer reagent. This synthetic strategy offers several outstanding features, including simplicity of operation, absence of transition metals and chemical oxidants, and high tolerance towards diverse functional groups. A variety of primary, secondary amines, and quinoxalinones can be tolerated, leading to the formation of secondary and tertiary amination products in good to excellent yields.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Heng Li, Congcong Qiang, Yujie Liao, Qiao Chu, Ping Liu, Peipei Sun
Summary: In this study, a method for electrochemical cross dehydrogenative coupling (CDC) reaction of heterocycles with ethers mediated by hydrogen atom transfer (HAT) was established. Saturated linear, branched or cyclic ethers were all suitable for this cross-coupling reaction, resulting in the formation of the corresponding products in yields of 70-98%. The advantages of this reaction include transition metal- and chemical oxidant-free conditions, high yields, and broad functional group tolerance, etc.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Ravichandran Logeswaran, Masilamani Jeganmohan
Summary: This paper reports an oxidative cross-coupling reaction between α,β-unsaturated compounds and unactivated alkenes via cobalt-catalyzed vinylic C-H activation. The reaction was investigated with differently functionalized unsaturated compounds and unactivated olefins, leading to the preparation of valuable amide functionalized butadienes and indenones in good yields. A possible reaction mechanism involving directed olefinic C-H activation through a base-assisted deprotonation pathway is proposed.
Article
Chemistry, Organic
Peng Yang, Xia Wang, Liang Wang, Jiahua He, Qian Zhang, Dong Li
Summary: A novel metal-free C-N bond formation method was developed through oxidative cross-dehydrogenative coupling between iodoarenes and acylanilides, mediated by mCPBA. The reaction exhibited high para-selectivity with retention of the iodine atom, enabling further transformations. This method is characterized by substrate availability, easy operation, and atom economy, providing a simple and efficient route for the preparation of functionalized N-aryl amides.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Xin Han, Chenxing Guo, Chen Xu, Linlin Shi, Binghui Liu, Zhe Zhang, Qixia Bai, Bo Song, Fangfang Pan, Shuai Lu, Xinju Zhu, Heng Wang, Xin-Qi Hao, Mao-Ping Song, Xiaopeng Li
Summary: We have successfully designed and synthesized two series of metallo-supramolecular octahedral cages based on the self-assembly of modified tripyridyl ligands. These cages have good water solubility and are capable of mediating visible-light-promoted reactions.
Article
Chemistry, Organic
Xinyan Li, Xiulan Shao, Xiaoyu Zhang, Qiaoyue Zhao, Hongtao Lai, Bing Cui, Zhihui Shao, Mingqin Zhao
Summary: This study reports an efficient green method for synthesizing carbonyl furan derivatives by dehydrogenative coupling reaction. The reaction is performed under mild reaction conditions with the presence of catalyst and base, resulting in the successful synthesis of various derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Xiao-lin Cui, Hao-yu Tian, Shuo-jin Wang, Xun Chen, Du-lin Kong
Summary: A regioselective metal-free sulfenylation of imidazoheterocycles with heterocyclic thiols or thiones has been achieved using a cross-dehydrogenative coupling method in water. The procedure offers advantages such as green solvents, absence of foul-smelling sulfur sources, and mild conditions, making it highly applicable in the pharmaceutical industry.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Keisho Okura, Hitomi Kawashima, Fumiko Tamakuni, Naoya Nishida, Eiji Shirakawa
CHEMICAL COMMUNICATIONS
(2016)
Article
Chemistry, Organic
Keisho Okura, Eiji Shirakawa
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Ryota Ueno, Takashi Shimizu, Eiji Shirakawa
Article
Chemistry, Organic
Ryota Ueno, Yuko Ikeda, Eiji Shirakawa
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Keisho Okura, Tsuyoshi Teranishi, Yuto Yoshida, Eiji Shirakawa
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Kazuya Kiriyama, Keisho Okura, Fumiko Tamakuni, Eiji Shirakawa
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Multidisciplinary
Yuko Ikeda, Ryota Ueno, Yuto Akai, Eiji Shirakawa
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Multidisciplinary
Eiji Shirakawa, Keisho Okura, Nanase Uchiyama, Takuya Murakami, Tamio Hayashi
Article
Chemistry, Organic
Eiji Shirakawa
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2019)
Article
Chemistry, Multidisciplinary
Goki Hirata, Kentarou Takeuchi, Yusuke Shimoharai, Michinori Sumimoto, Hazuki Kaizawa, Toshiki Nokami, Takashi Koike, Manabu Abe, Eiji Shirakawa, Takashi Nishikata
Summary: This paper describes the reaction of tertiary alkyl alcohols and non-chiral or chiral alpha-bromocarboxamides as a source for the formation of congested ether compounds possessing two different tertiary alkyl groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Yuko Ikeda, Yuko Matsukawa, Kyohei Yonekura, Eiji Shirakawa
Summary: By utilizing a substoichiometric amount of a tert-butoxy radical precursor and a base, alkylamides can be heteroarylated at their alpha-C-H bonds with sulfonylheteroarenes through a radical chain reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
Eiji Shirakawa, Yuki Ota, Kyohei Yonekura, Keisho Okura, Sahiro Mizusawa, Sujan Kumar Sarkar, Manabu Abe
Summary: An electron has been found to catalyze the cross-coupling reaction of organometallic compounds with aryl halides, which is more desirable for green and sustainable chemistry compared to transition metal catalysis. However, high temperature is required for this electron catalysis. We discovered that visible light photoirradiation can accelerate the electron-catalyzed reaction by using photoredox catalysis, enabling the reaction to proceed at room temperature. The supply of the electron catalyst through photoredox catalysis also expands the scope of aryl halides.
Article
Chemistry, Organic
Kyohei Yonekura, Mari Murooka, Kohei Aoki, Eiji Shirakawa
Summary: The electrochemical a-arylation of alkylamines with sulfonylarenes has been developed, allowing for the synthesis of a variety of a-arylalkylamines. Mechanistic studies demonstrate that anodic oxidation of an alkylamine with a sulfinate as a mediator followed by deprotonation produces an a-aminoalkyl radical, which undergoes homolytic aromatic substitution on a sulfonylarene, giving the corresponding a-arylalkylamine.
Article
Chemistry, Multidisciplinary
Kazuya Kiriyama, Eiji Shirakawa
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)
