Article
Chemistry, Organic
Heping Tan, Changmei Zhang, Yangling Deng, Mengxuan Zhang, Xiya Cheng, Jie Wu, Danqing Zheng
Summary: A direct C(sp3)-H sulfinylation reaction of alkanes with sulfinyl sulfones via decatungstate photocatalysis is presented. The sulfinyl sulfones generated in situ from sulfinates can react with alkyl radicals produced through photoinduced direct hydrogen atom transfer, resulting in a variety of sulfoxides. This radical sulfinylation process provides an efficient and concise method for synthesizing sulfoxides from abundant alkanes under mild conditions. Additionally, aldehydes can also be transformed into corresponding sulfoxides through decarbonylative sulfinylation using the same strategy.
Article
Chemistry, Multidisciplinary
Dat Phuc Tran, Yuki Sato, Yuki Yamamoto, Shin-ichi Kawaguchi, Shintaro Kodama, Akihiro Nomoto, Akiya Ogawa
Summary: A series of bifunctional phosphine compounds as potential γ-functionalized phosphine ligand precursors are conveniently synthesized by radical addition under photoirradiation, with good regioselectivity and ease of operation.
RESEARCH ON CHEMICAL INTERMEDIATES
(2021)
Article
Chemistry, Organic
Yaling Xu, Xueying Zhou, Luya Chen, Yunfei Ma, Ge Wu
Summary: The copper-catalyzed radical multi-component coupling enables the rapid synthesis of a library of aminophosphinoylated maleimides. This method is applicable to clinical drug molecules containing sulfonamide and arylamine functional groups, allowing access to sterically congested products. It shows good functional group tolerance and can be used on a wide range of substrates.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Editorial Material
Chemistry, Multidisciplinary
Yi Wei, Fen-Ya Xiong, Liang-Qiu Lu, Wen-Jing Xiao
Summary: In this paper, Gevorgyan et al. described a photoinduced palladium catalysis method that enables the direct allylic C-H amination of alkenes, including internal ones. This strategy overcomes a major challenge in chemical synthesis and offers excellent selectivities.
Article
Chemistry, Organic
Shengkun Guo, Xiaoyu Shen, Xiaoyun Chen, Huaguang Yu, Ying Han, Chaoguo Yan, Yaocheng Shi, Hong Hou, Shaoqun Zhu
Summary: This study presents a photoinduced copper-catalyzed 1,2-difunctionalization of 1,3-dienes. The generation of selenium atom radicals through visible light irradiation of diselenides leads to radical addition with 1,3-dienes, resulting in the formation of allyl radical intermediates. Rapid Z/E isomerization enables thermodynamically favorable intermediate formation, facilitating copper-catalyzed stereoselective functionalization with different nucleophiles.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yusuke Masuda, Hiromu Tsuda, Masahiro Murakami
Summary: This unique photoinduced reaction couples a triarylphosphine, an alkene, and water to produce a novel compound, increasing molecular complexity and applicability to the Wittig olefination reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Guo-Qing Li, Fan-Rong Meng, Wen-Jing Xiao, Jia-Rong Chen
Summary: Catalytic radical difunctionalization of 1,3-enynes is a promising method for constructing valuable allenes and propargylic compounds. However, there has been limited progress in enantioselective radical 1,2-difunctionalization. In this study, a regio- and enantioselective radical three-component coupling of 1,3-enynes, oxime esters, and carboxylic acids through photoinduced copper catalysis is reported. This protocol demonstrates excellent enantioselectivity and provides access to a library of cyanoalkylated propargylic esters.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Guoxiang Zhang, Hui He, Xiaoxiao Chen, Shao-Fei Ni, Rong Zeng
Summary: The traditional photoinduced anti-Markovnikov hydroamination of olefins requires high oxidative ability photocatalysts to initiate the single-electron process. However, in this study, we used an inexpensive reagent, bis(2,4,6-triisopropylphenyl) disulfide, with relatively low oxidative ability, as a photo and hydrogen atom transfer catalyst to achieve intramolecular hydroamination. The mechanistic studies and DFT calculations support a novel process involving N centered radical generation through the homolysis of the in situ formed N-S species, followed by cyclization. Various nitrogen-containing cycles can be obtained.
Article
Chemistry, Organic
Wanqing Zuo, Lingling Zuo, Xiao Geng, Zhifang Li, Lei Wang
Summary: In this study, a photoinduced three-component coupling/cyclization reaction was reported for the de novo synthesis of 1,3,4-oxdiazole- or benzothiazole-functionalized enamines via quadruple cleavage of CF2Br2. This reaction provides an efficient and general approach for the C-H heteroarylation of enamines, utilizing a new reactivity of CF2Br2 as the C1 source.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Bin Lu, Zhihan Zhang, Min Jiang, Dong Liang, Zi-Wei He, Feng-Shuo Bao, Wen-Jing Xiao, Jia-Rong Chen
Summary: A visible-light-driven radical relay five-component double aminocarbonylation reaction of alkenes is described for direct access to valuable γ-trifluoromethyl α-ketoamides with good yields and selectivities. Crucial was the identification of distinct dual roles of the amine coupling partners, which sequentially act as electron donors for the formation of photoactive electron donor-acceptor complexes with radical precursors and then as a CO acceptor to form carbamoyl radicals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Hong Hou, Bing Zhou, Jiawei Wang, Dengyang Zhao, Duhao Sun, Xiaoyun Chen, Ying Han, Chaoguo Yan, Yaocheng Shi, Shaoqun Zhu
Summary: A stereo- and regioselective cis-hydrophosphorylation reaction of internal alkyne of 1,3-enynes is described, which allows access to various 1,3-dienes in good yields. Visible-light irradiation of NiCl2(PPh3)(2) enables the generation of highly reactive nickel(II)-phosphorus species to facilitate the reaction under mild conditions.
Article
Chemistry, Multidisciplinary
Weijie Deng, Yunfei Hu, Jinhui Hu, Xinling Li, Yibiao Li, Yubing Huang
Summary: A metal-free electrochemically induced strategy has been developed for the regioselective hydro/deuterophosphonylation of electron-rich alkenes with P(O)H compounds, providing various Markovnikov-type adducts in high yields. Monodeuterated organophosphorus compounds with high deuterium incorporation can be obtained by adding D2O as the D source. The protocol offers broad substrate scope, low energy consumption, high atom economy, and scalability.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Jun Chen, Yu-Jie Liang, Peng-Zi Wang, Guo-Qing Li, Bin Zhang, Hao Qian, Xiao-Die Huan, Wei Guan, Wen-Jing Xiao, Jia-Rong Chen
Summary: This study presents a photoinduced copper-catalyzed cross-coupling reaction for the generation of allylic esters. The reaction proceeds at room temperature with high regio- and enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Pei-shang Li, Qiao-qiao Teng, Ming Chen
Summary: Described here is a redox-neutral palladium-catalyzed photo-induced radical cascade domino Heck reaction between N-aryl acrylamide and vinyl arenes. A variety of bioactive oxindoles with an all-carbon quaternary center were synthesized. The reaction proceeds via an open-shell intermediate and occurs under mild reaction conditions, showing excellent functional group tolerance. Importantly, the synthesized products can be readily transformed into biologically active molecules, including (& PLUSMN;)-physostigmine and (& PLUSMN;)-physovenine.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Yu-Shi Jiang, Shan-Shan Li, Xue-Ling Luo, Li-Ning Chen, Dan-Na Chen, Peng-Ju Xia
Summary: A metal-free difunctionalization strategy for diazenes was developed using bifunctionalization reagents, leading to the construction of over 30 triazane core motifs. This strategy involves a unique N(sp(3))-N(sp(2)) radical coupling between the hydrazine radical and the imine radical, allowing the efficient installation of imines and various functional groups on both ends of the nitrogen-nitrogen bond of diazenes.
Article
Chemistry, Multidisciplinary
Yuki Sato, Shin-ichi Kawaguchi, Akihiro Nomoto, Akiya Ogawa
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Organic
Cong Chi Tran, Shin-ichi Kawaguchi, Yohsuke Kobiki, Hitomi Matsubara, Dat Phuc Tran, Shintaro Kodama, Akihiro Nomoto, Akiya Ogawa
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Review
Chemistry, Organic
Yuki Yamamoto, Shin-ichi Kawaguchi, Shintaro Kodama, Akihiro Nomoto, Akiya Ogawa
CURRENT ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Cong Chi Tran, Shin-ichi Kawaguchi, Fumiya Sato, Akihiro Nomoto, Akiya Ogawa
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Tsuyoshi Douchi, Masahiro Akitake, Motohiro Sonoda, Yasumasa Sugiyama, Shinji Tanimori
SYNTHETIC COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Kento Tokumoto, Kouhei Makiyama, Motohiro Sonoda, Shinji Tanimori
Summary: The facile and general transition-metal-free access to 1-substituted-4-quinazolinones was achieved through proline-mediated cyclization, with potential pathways including radical intermediates and SNAr route. The gram-scale synthesis of 1-phenyl-4-quinazolinone was also successfully demonstrated without loss of efficiency.
Article
Chemistry, Physical
Shintaro Kodama, Yuki Yamamoto, Yohsuke Kobiki, Hitomi Matsubara, Cong Chi Tran, Shin-ichi Kawaguchi, Akihiro Nomoto, Akiya Ogawa
Summary: The study showed that the use of different transition metal catalysts can selectively synthesize different products, while also achieving a cascade synthesis from diarylation reactions to quinoxaline compounds.
Article
Biochemistry & Molecular Biology
Kento Sonoda, Saki Ujike, Akito Katayama, Norio Suzuki, Shin-ichi Kawaguchi, Tadayuki Tsujita
Summary: In this study, a higher lipophilic derivative of PyrzA was synthesized and evaluated, showing higher HIF activity and stabilizing ability at low concentrations compared to the commercially available HIF activator Roxadustat.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Motohiro Sonoda, Yusuke Mimura, Shizuki Noda, Atsushi Okazawa
Summary: Aryloxyacetylthiourea and its derivatives were synthesized using commercially available phenols, 2-chloroacetamide, and N-aryl isothiocyanates. The byproducts obtained in this process were found to have bioactive properties. A one-pot synthesis method for PI-28 derivatives with comparable overall yields was also developed.
Correction
Chemistry, Medicinal
Kento Sonoda, Sudarma Bogahawaththa, Akito Katayama, Saki Ujike, Sae Kuroki, Naho Kitagawa, Kohichi Hirotsuru, Norio Suzuki, Toshio Miyata, Shin-ichi Kawaguchi, Tadayuki Tsujita
ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE
(2022)
Article
Chemistry, Medicinal
Kento Sonoda, Sudarma Bogahawatta, Akito Katayama, Saki Ujike, Sae Kuroki, Naho Kitagawa, Kohichi Hirotsuru, Norio Suzuki, Toshio Miyata, Shin-ichi Kawaguchi, Tadayuki Tsujita
Summary: HIF-alpha activation has shown promising results in treating ischemic diseases. Many existing activators stabilize HIF-alpha by displacing 2-OG from PHDs. However, their specificity is low. In this study, a novel HIF activator called PyrzA was identified, which does not contain a 2-OG scaffold. PyrzA enhances HIF-alpha stability and upregulates the expression of HIF target genes. Interestingly, PyrzA decreases HIF-1 alpha prolyl hydroxylation, suggesting a novel mechanism for HIF activation.
ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE
(2022)
Article
Chemistry, Organic
Takahito Uemura, Yusuke Saito, Motohiro Sonoda, Shinji Tanimori
Summary: Equol, a nonsteroidal estrogen, has been synthesized in enantioenriched forms based on MacMillan's alpha-arylation of carbonyl compound mediated by amino acid derived indazolidinones and copper precatalysts. The natural form of (S)-equol and its enantiomer (R)-equol have been successfully synthesized from 2,4-dimethoxybenzaldehyde with good enantiomeric purity (90% ee and 90% ee, respectively).
Article
Chemistry, Organic
Yuki Yamamoto, Shin-ichi Kawaguchi, Misaki Nishimura, Yuki Sato, Yoshihisa Shimada, Akihiro Tabuchi, Akihiro Nomoto, Akiya Ogawa
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Yuki Yamamoto, Ryo Tanaka, Miyuto Ota, Misaki Nishimura, Cong Chi Tran, Shin-ichi Kawaguchi, Shintaro Kodama, Akihiro Nomoto, Akiya Ogawa
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Haruna Nariki, Takuya Miyamura, Daiki Matsui, Motohiro Sonoda, Shinji Tanimori
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)
