Article
Chemistry, Organic
Xue-Ling Luo, Miao-Sha Huang, Shan-Shan Li, Yu-Shi Jiang, Li-Ning Chen, Shu-Hui Li, Peng-Ju Xia
Summary: In this study, a strategy was developed using commercially available alkyl iodides and O-benzoyl oxime to efficiently introduce alkyl and iminyl groups via energy transfer and halogen-atom transfer processes. Three-component 1,2-carboimination of olefins and four-component 1,4-carboimination across olefins and alkynes were performed, resulting in the synthesis of over 60 nitrogen-containing molecules. Moreover, this transformation enables the synthesis of molecules with sensitive groups that were previously difficult to achieve.
Article
Chemistry, Organic
Votarikari Dinesh, Rajagopal Nagarajan
Summary: This study presents a direct metal- and oxidant-free photochemical decarboxylative formylation of indoles using 50% aqueous glyoxylic acid, resulting in good to moderate yields.
Article
Chemistry, Organic
Randolph A. Escobar, Jeffrey W. Johannes
Summary: This study presents a reductive radical conjugate addition that activates alkyl bromides via cobalt/iridium catalysis to form alkyl radicals, with a broad substrate scope including benzylic halides and halides containing free alcohols, silanes, and chlorides.
Article
Chemistry, Multidisciplinary
Xue-Gong Jia, Qi-Wei Yao, Xing-Zhong Shu
Summary: This study presents a new method for the preparation of enantioenriched heterocycles through N-cyclization-alkylation reaction, addressing a long-standing challenge in the synthetic community and achieving highly enantioenriched pyrrolines under mild conditions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Andrey Shatskiy, Markus D. Karkas
Summary: Recent progress has been made in accessing unnatural alpha-amino acids through photoredox-mediated synthetic methods with a focus on various decarboxylative radical-based strategies.
Article
Chemistry, Multidisciplinary
Jonathan D. Bell, Iain Robb, John A. Murphy
Summary: Highly selective photocatalytic functionalisations of alkyl groups in aryl alkyl ethers have been achieved using a phosphate-based acridinium catalyst and visible light irradiation. The reaction proceeds through direct single-electron oxidation and subsequent deprotonation steps, resulting in a wide range of functionalised products in good to excellent yield.
Article
Chemistry, Organic
Minjie Zhang, Peng Cui, Kai Zhang, Zhen Shi, Xu Cheng, Xiang Ji, Hao Song, Bowen Ke, Yong Qin
Summary: An efficient method for the Ir-catalyzed asymmetric hydrogenation of tetrasubstituted alpha-acylpyrazole-beta-alkyl cycloalkenes has been developed, affording 1,2-cis substituted carbo- or heterocycles with high yields and excellent enantioselectivities.
ORGANIC CHEMISTRY FRONTIERS
(2023)
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)
Review
Biochemistry & Molecular Biology
Beatrice Quiclet-Sire, Samir Z. Zard
Summary: The preparation and use of alpha-(acyloxy)alkyl xanthates for generating and capturing alpha-(acyloxy)alkyl radicals are reviewed. The article describes their inter- and intramolecular additions to various alkenes and aromatic rings, as well as their radical allylation and vinylation reactions. The application of these reactions in the total synthesis of two 4-hydroxytetralone natural products is also presented.
Article
Chemistry, Multidisciplinary
Hongxiao Li, Qianqian Sun, TianTian Zhang, Yunrong Chen, Jianhua Zhang, Hongmei Deng, Haizhen Jiang
Summary: An efficient and convenient method for the synthesis of allylic difluorides has been developed. The reaction demonstrated good functional-group tolerance, broad substrate scope, and excellent diastereoselectivity.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
Young Woo Kang, Ran Hui Kim, Shafrizal Rasyid Atriardi, Sang Kook Woo
Summary: We developed a photocatalyzed Giese reaction method that overcomes the substrate scope limitations and shows good functional groups tolerance, achieving high yields. The reaction mechanism involves in situ generation of an alkoxymethyl radical via single-electron oxidation of alpha-trimethylsilyl-substituted ethers.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yue Dong, Xiang Meng, Giri Gnawali, Mengyang Chang, Wei Wang
Summary: A photoredox catalytic asymmetric method is developed to introduce both aliphatic and aromatic side chains and deuterium into chiral methyleneoxazolidinone simultaneously. The coupling of readily available boronic acids with the chiral auxiliary yields structurally diverse alpha-deuterated alpha-amino acid derivatives with high diastereoselectivity and deuteration.
Article
Chemistry, Organic
Fengxiang Zhu, Pengpeng Yin, Pengbo Zhang
Summary: A convenient four-component reaction has been developed to directly transform aryl iodides with alkyl halides into aromatic esters and diesters via palladium-catalyzed carbonylation with water as solvent. The method exhibits moderate to good yields and broad functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Wenqiang Mei, Yilin Kong, Guobing Yan
Summary: This review systematically summarizes the decarboxylative functionalization of alpha,alpha-difluoroarylacetic acids and salts, discussing their mechanisms.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Ling Yang, Dong-Hang Tan, Wen-Xin Fan, Xu-Ge Liu, Jia-Qiang Wu, Zhi-Shu Huang, Qingjiang Li, Honggen Wang
Summary: A new method was proposed utilizing benzyl N-methyliminodiacetyl (MIDA) boronates for photochemical radical C-H halogenation, enabling successful fluorination, chlorination, and bromination reactions. The resulting brominated product could be further transformed into a variety of organic compounds, including those difficult to form with alpha-halo sp(2)-B boronate esters, by reaction with different nucleophiles. An activation effect of the B(MIDA) moiety was discovered.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Yasuharu Yoshimi
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
(2017)
Article
Chemistry, Organic
Mugen Yamawaki, Yoshiki Okita, Takashi Yamamoto, Toshio Morita, Yasuharu Yoshimi
Article
Chemistry, Multidisciplinary
Y. Iwata, Y. Tanaka, S. Kubosaki, T. Morita, Y. Yoshimi
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Organic
Takashi Yamamoto, Tomoya Iwasaki, Toshio Morita, Yasuharu Yoshimi
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Yosuke Tanaka, Suzuka Kubosaki, Kazuyuki Osaka, Mugen Yamawaki, Toshio Morita, Yasuharu Yoshimi
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Tomoya Iwasaki, Yuka Tajimi, Kenta Kameda, Callum Kingwell, William Wcislo, Kazuyuki Osaka, Mugen Yamawaki, Toshio Morita, Yasuharu Yoshimi
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Kazuyuki Osaka, Ayuka Usami, Tomoya Iwasaki, Mugen Yamawaki, Toshio Morita, Yasuharu Yoshimi
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Yui Ozaki, Tomoaki Yamada, Taisei Mizuno, Kazuyuki Osaka, Mugen Yamawaki, Hajime Maeda, Toshio Morita, Yasuharu Yoshimi
Article
Biochemistry & Molecular Biology
Mugen Yamawaki, Akiko Asano, Toshiki Furutani, Yuki Izumi, Yosuke Tanaka, Kazuyuki Osaka, Toshio Morita, Yasuharu Yoshimi
Article
Chemistry, Organic
Suzuka Kubosaki, Haruka Takeuchi, Yutaka Iwata, Yosuke Tanaka, Kazuyuki Osaka, Mugen Yamawaki, Toshio Morita, Yasuharu Yoshimi
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Yuka Tajimi, Yasuhiro Nachi, Ryoko Inada, Ryoga Hashimoto, Mugen Yamawaki, Kei Ohkubo, Toshio Morita, Yasuharu Yoshimi
Summary: Visible-light-induced decarboxylative and deboronative reactions were achieved using two-molecule organic photoredox catalysts. The high solubility improved reaction efficiency and product yield. The oxidation potential of the electron-donor molecule can be tuned for a wide range of substrates.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yudai Shinkawa, Toshiki Furutani, Takumi Ikeda, Mugen Yamawaki, Toshio Morita, Yasuharu Yoshimi
Summary: The side-chain functionalization of aspartic/glutamic acid derivatives was achieved through photoinduced decarboxylation using organic two-molecule photoredox catalysts without racemization under mild conditions. A facile process involving the preparation of substrates and photoinduced decarboxylative radical additions provides easy access to the linked amino acids with carbohydrates and amino acids at the side chain.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Mugen Yamawaki, Ryoga Hashimoto, Yuki Kawabata, Miwa Ichihashi, Yasuhiro Nachi, Rinpei Inari, Chisato Sakamoto, Toshio Morita, Yasuharu Yoshimi
Summary: In this study, visible-light-induced decarboxylative and deboronative radical addition of aliphatic carboxylic acids and arylboronic acid pinacol esters to electron-deficient alkenes was efficiently achieved using two-molecule organic photoredox catalysts. The reaction generated alkyl and aryl radicals to form radical adducts. The presence of a base and substrate played important roles in this photochemical system, and the sequential photoinduced decarboxylation of glutamic acid with two different carboxy groups was successfully carried out.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ryoga Hashimoto, Toshiki Furutani, Hirotsugu Suzuki, Yasuharu Yoshimi
Summary: In this study, the effects of electron-donors and counter-cations on the visible-light-induced deboronation and decarboxylation of arylboronic acid derivatives and benzoic acids were investigated using two-molecule photoredox catalysts. Different efficiencies in aryl radical generation were observed upon replacing the electron-donor and counter-cation. The rate of photoinduced deboronation of arylboronic acid derivatives strongly depends on the substituent, whereas the influence of counter-cation (Na* and K*) was relatively minor. In the case of the benzoate ion derived from benzoic acid, the effect of both substituent and counter-cation decreases because of the complex mechanism. Additionally, the dependence of the oxidation ability of the radical cation on the electron-donor suggests the possibility of roughly estimating the oxidation potentials of the arylborate and benzoate ions.
Article
Chemistry, Multidisciplinary
Yasuharu Yoshimi
Summary: Based on our recent results, this article explores the distinct reactivities of two-molecule photoredox systems compared to one-molecule photoredox systems. The inefficient electron transfer processes in the two-molecule system result in unique products through different pathways. The substitution of photoredox catalysts with appropriate oxidation/reduction potentials in this system provides valuable insights into photoredox reactions.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
