Article
Chemistry, Organic
Elena Shaitanova, Vaclav Matousek, Tadeas Herentin, Martin Adamec, Robert Matyas, Blanka Klepetarova, Petr Beier
Summary: This article introduces a new method for preparing fluorinated azidoethane and its application in various reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Akanksha M. Pandey, Shankhajit Mondal, Boopathy Gnanaprakasam
Summary: Continuous-flow reactors are an ideal tool for synthesizing potentially explosive but synthetically useful organic substances. This study reports the continuous-flow direct azidation of alcohols using TMSN3 as a transfer reagent and Amberlyst-15 as a recyclable catalyst. The study also explores the application of continuous-flow reactors in other organic reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Xue Liu, Xinyi Li, Long Liu, Tianzeng Huang, Wenhao Chen, Michal Szostak, Tieqiao Chen
Summary: The direct acyl Sonogashira cross-coupling of carboxylic acids with terminal alkynes has been achieved through Pd/Cu cooperative catalysis, offering a method to prepare ynones directly from carboxylic acids. The reaction shows high chemoselectivity, functional group tolerance, and good to high yields of ynones. It has synthetic value in organic synthesis, demonstrated by late-stage modification of bioactive molecules and gram-scale experiments.
Article
Chemistry, Organic
Thomas Abegg, Janine Cossy, Christophe Meyer
Summary: cis-1,2-Dialkenylcyclopropanes with a vinyl azide group were generated by Knoevenagel condensations and underwent cascade Cope and Winstein [3,3]-sigmatropic rearrangements under mild conditions. This reaction sequence allows for the synthesis of diversely substituted 1,4-cycloheptadienes with a secondary allylic azide containing up to three stereocenters.
Article
Chemistry, Organic
Caria Evans, William J. Berkey, Christopher W. Jones, Stefan France
Summary: A Zr-catalyzed synthesis of tetrasubstituted 1,3-diacylpyrroles has been reported using N-acyl alpha-aminoaldehydes and 1,3-dicarbonyl compounds. The reaction showed high yields (up to 88%) and the products were found to be hydrolytically and configurationally stable. The N-acyl alpha-aminoaldehydes were easily prepared from corresponding alpha-amino acids. The reaction could accommodate various substrate types and a range of 1,3-dicarbonyls, including aldehyde derived from a l,l-dipeptide, an in situ generated aldehyde, and an N-acylated glucosamine.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Wen-Hao Cui, Wen-Biao Zhou, Zhiwen Ye, Ying He
Summary: In the past decade, energetic ionic compounds have gained significant research interest due to their relatively low sensitivities compared to covalent compounds. However, the synthesis of these compounds has been mostly limited to the design of anionic moieties. This study presents a practical synthesis of 3,4-diamino-6-azido-1H-pyrazolo[4,3-c]pyridin-5-ium energetic ionic compounds, which exhibit good detonation performances and low sensitivities. This synthetic strategy could be applied to the synthesis of fused pyridinyl azides, highlighting its importance in the field of heterocyclic chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yumeng Liang, Zhengyu Zhao, Akihito Taya, Norio Shibata
Summary: A novel reagent system allows for the direct synthesis of acyl fluorides from carboxylic acids, aldehydes, or alcohols with high yields up to 99%. This transformation is useful for late-stage functionalization of natural products and drug molecules containing a carboxylic acid, aldehyde, or alcohol group.
Review
Chemistry, Organic
Ryan Moreira, Michael Noden, Scott D. Taylor
Summary: Azido acids are important synthon for the synthesis of complex peptides, offering advantages in the synthesis of branched and/or cyclic peptides. They are less bulky than urethane-protected counterparts and react effectively in coupling reactions of difficult-to-form peptide and ester bonds.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Xiu Wang, Fei Wang, Fengfeng Huang, Chuanfa Ni, Jinbo Hu
Summary: 3,3-Difluoro-1,2-diphenylcyclopropene (CpFluor), as a bench-stable fluorination reagent, has been developed for the deoxyfluorination of carboxylic acids to afford various acyl fluorides. This all-carbon-based fluorination reagent enables the efficient transformation of (hetero)aryl, alkyl, alkenyl, and alkynyl carboxylic acids to the corresponding acyl fluorides under neutral conditions, and features the synthesis of acyl fluorides with in-situ formed CpFluor and the one-pot amidation reaction of carboxylic acids via in-situ formed acyl fluorides.
Article
Chemistry, Organic
Joshua M. Kofsky, Gour C. Daskhan, Matthew S. Macauley, Chantelle J. Capicciotti
Summary: A new method for synthesizing azido sugars using fluorosulfuryl azide (FSO2N3) and a Cu(II) catalyst as a diazotransfer reagent is reported. The method allows for the conversion of hexosamine substrates to azido sugars in less than 5 minutes with quantitative yield, without the need for harsh conditions or long reaction times. The method is also applicable to other amino sugar derivatives and is orthogonal to O-sulfation.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xue-Qing Mou, Min Wang, Liang-Chen Ren, Yu-Rui Jian, Xin-Yu Fu, Hong-Yu Zheng, Xiao Zha, Bao-Dong Cui, Yun Zhang, Yong-Zheng Chen
Summary: A general photoredox-catalyzed intramolecular oxy- and aminoacylation of internal alkenes with acyl oxime esters to access various acyl heterocycles is developed.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Feng Jiang, Tengfei Meng, Ying Zhou, Zhenying Xiong, Yupei Zhao, Wengang Guo
Summary: We report an enantio- and diastereodivergent synthesis of enantioenriched fluorenes with broad substrate scope and high enantioselectivity (up to 99% ee) under low catalyst loading (0.1 mol %). The success of this method lies in the pseudo-diastereodivergent desymmetrization of stereoisomers of meso-epoxides enabled by the same organocatalyst. Furthermore, some of the chiral fluorenes obtained exhibit high fluorescence quantum yields (up to 76.6%), as evidenced by photophysical properties studies.
Article
Chemistry, Organic
Jin Zhang, Pei Zhang, Yangmin Ma, Michal Szostak
Summary: This study reports a novel solvent-free method for synthesizing ketones with high selectivity from acyl chlorides and boronic acids. The reaction takes place in the solid state, without the use of solvents, and has a short reaction time, demonstrating excellent selectivity for C(acyl)-Cl bond cleavage.
Article
Chemistry, Multidisciplinary
Ranjit S. Atapalkar, Amol A. Kulkarni
Summary: A simple and efficient solvent-free protocol for continuous flow synthesis of amides at room temperature is developed using easily available starting materials. N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC.HCl) was used as the reagent for the formation of an amide bond without using any metal catalyst or additives. This approach is extended for the synthesis of 36 derivatives and 2 bioactive molecules using different substrates.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Yiping Li, Jingyue Li, Guangjun Bao, Changjun Yu, Yuyang Liu, Zeyuan He, Peng Wang, Wen Ma, Junqiu Xie, Wangsheng Sun, Rui Wang
Summary: In this study, a novel coupling reagent NDTP was explored, which exhibited mild, nonirritating, convenient availability, and recyclability. It could activate carboxylic acids via acyl thiocyanide and enable the rapid synthesis of amides and peptides under mild conditions. Furthermore, the methodology was compatible with Fmoc-SPPS, providing an alternative approach for peptide manufacturing.
Article
Biochemistry & Molecular Biology
Md. Monirul Islam, Satoshi Fujii, Shinobu Sato, Tatsuo Okauchi, Shigeori Takenaka
BIOORGANIC & MEDICINAL CHEMISTRY
(2015)
Article
Chemistry, Physical
Tetsuji Moriguchi, Naoya Kitou, Venkataprasad Jalli, Kenji Yoza, Shuichi Nagamatsu, Tatsuo Okauchi, Akihiko Tsuge, Wataru Takashima
JOURNAL OF MOLECULAR STRUCTURE
(2016)
Article
Chemistry, Organic
Mitsuru Kitamura, Hiroaki Fukuma, Mitsuaki Kobayashi, Shinya Okayama, Tatsuo Okauchi
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Mitsuru Kitamura, Akihiro Ishikawa, Tatsuo Okauchi
TETRAHEDRON LETTERS
(2016)
Article
Chemistry, Physical
Tetsuji Moriguchi, Makoto Higashi, Daisuke Yakeya, Venkataprasad Jalli, Akihiko Tsuge, Tatsuo Okauchi, Shuichi Nagamatsu, Wataru Takashima
JOURNAL OF MOLECULAR STRUCTURE
(2017)
Article
Chemistry, Organic
Dina I. A. Othman, Kota Otsuka, Shuhei Takahashi, Khalid B. Selim, Magda A. El-Sayed, Atif S. Tantawy, Tatsuo Okauchi, Mitsuru Kitamura
Article
Chemistry, Organic
Mitsuru Kitamura, Kota Otsuka, Shuhei Takahashi, Tatsuo Okauchi
TETRAHEDRON LETTERS
(2017)
Article
Chemistry, Multidisciplinary
Shuhei Takahashi, Hirokazu Shimooka, Tatsuo Okauchi, Mitsuru Kitamura
Article
Biochemistry & Molecular Biology
Dina I. A. Othman, Khalid B. Selim, Magda A. -A. El-Sayed, Atif S. Tantawy, Yhiya Amen, Kuniyoshi Shimizu, Tatsuo Okauchi, Mitsuru Kitamura
BIOORGANIC & MEDICINAL CHEMISTRY
(2019)
Article
Chemistry, Organic
Mitsuru Kitamura, Kento Murakami, Tatsuya Koga, Takashi Eto, Akihiro Ishikawa, Hirokazu Shimooka, Tatsuo Okauchi
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Kouta Tsubaki, Hirokazu Shimooka, Mitsuru Kitamura, Tatsuo Okauchi
Article
Chemistry, Organic
Mitsuru Kitamura, Ryo Fujimura, Tomoaki Nishimura, Shuhei Takahashi, Hirokazu Shimooka, Tatsuo Okauchi
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Mitsuru Kitamura, Tomoaki Nishimura, Kota Otsuka, Hirokazu Shimooka, Tatsuo Okauchi
TETRAHEDRON LETTERS
(2020)
Article
Chemistry, Medicinal
Kouta Tsubaki, Matthew L. Hammill, Andrew J. Varley, Mitsuru Kitamura, Tatsuo Okauchi, Jean-Paul Desaulniers
ACS MEDICINAL CHEMISTRY LETTERS
(2020)
Article
Biochemistry & Molecular Biology
Tatsuo Okauchi, Shuya Nakamura, Kouta Tsubaki, Momoko Asakawa, Mitsuru Kitamura
CARBOHYDRATE RESEARCH
(2017)