Article
Chemistry, Physical
Feng Zhong, Wen-Jun Yue, Xing-Hao Yin, Hong-Ming Zhang, Liang Yin
Summary: A copper(I)-catalyzed alkynylogous Mannich-type reaction is developed to provide chiral alpha-allenylamine derivatives in high selectivities. Additionally, a copper(I)-catalyzed cascade cyclization yields chiral beta-lactams containing a pyrazole moiety in high enantioselectivity. The synthetic utility and versatility of the alkynylogous product are demonstrated.
Article
Chemistry, Organic
Cunzhi Chen, Shuyan Fang, Mingwu Yu, Jiaxi Xu, Zhanhui Yang
Summary: In this study, tetrasubstituted thiophenes were produced in a redox-neutral manner through site-specific and regio-selective transannulation of Allenoates with 1,2,3-thiadiazoles in the presence of catalytic Rh(i)/bisphosphine. The 1,2,3-thiadiazoles act as masked 1,3-dipoles with nucleophilic sulfur and electrophilic carbon termini.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Rahul K. Shukla, Atul K. Chaturvedi, Chandra M. R. Volla
Summary: A Pd(II)-catalyzed directed, regio-controlled hydroheteroarylation of unactivated alkenes has been developed for the construction of gamma-heteroaryl-substituted carbonyl compounds. The methodology is operationally simple and compatible with a variety of nucleophiles to deliver structurally divergent heterocyclic skeletons. This approach also demonstrated synthetic utility in gram-scale synthesis, directing group removal, and late-stage modification of drugs and natural products.
Article
Chemistry, Organic
Kazutaka Kanayama, Ayumi Sawada, Katsushi Suda, Tetsuaki Fujihara
Summary: Regioselective sila-acylation and silaformylation of 1,3-dienes using a copper catalyst and silylborane as a silyl source resulted in the synthesis of β,γ-unsaturated ketones and aldehydes with a (dimethylphenyl-silyl)methyl moiety at the α-position, respectively.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Hitomi Tsuno, Jingfeng Shen, Hiroki Komatsu, Norihito Arichi, Shinsuke Inuki, Hiroaki Ohno
Summary: A gold-catalyzed cascade cyclization of naphthalene-tethered allenynes leads to strained fused phenanthrene derivatives. The reaction involves the nucleophilic reaction of an alkyne with an activated allene to generate a vinyl cation intermediate, followed by arylation with a tethered naphthalene ring to form the 4H-cyclopenta[def]phenanthrene (CPP) scaffold. The gold-catalyzed reaction of aryl-substituted substrates on the alkyne terminus also produces dibenzofluorene derivatives alongside the CPP derivatives, depending on the reaction conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Thi Minh Nguyet Trinh, Franck Schillinger, Sebastiano Guerra, Eric Meichsner, Iwona Nierengarten, Uwe Hahn, Michel Holler, Jean-Francois Nierengarten
Summary: A series of macrocyclic bis-malonates with different spacer units were used for regioselective functionalization of fullerene. By systematically modifying the spacers, fullerene bis-adducts with varied addition patterns were obtained. Finally, the bridging silylene groups were cleaved to yield acyclic fullerene bis-adducts with four alcohol functions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Khyarul Alam, Tian Li, I. F. Dempsey Hyatt, Mitchell P. Croatt
Summary: This study reports the regioselective intermolecular mono- or bis-hydroalkoxylation reactions of allenamides with alcohols under simple aluminum-catalyzed reaction conditions. Depending on the reaction conditions, the products can be N,O-acetals, gamma-substituted ethers, or 1,3-bis(alkoxy)propanamines. These reactions exhibit good functional group tolerance and efficiency.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kai Ji, Ka Lu, Jie Huang, Zi-Hao Li, Tong-Mei Ding, Zhi-Min Chen
Summary: A highly regio- and diastereo-selective Bronsted acid-catalyzed tandem hydrothiolation/Friedel-Crafts reaction of linear 1,3-dienes has been developed for the first time, providing a metal-free and atom-economic way of constructing thiochromane derivatives. Additionally, 4,3-addition hydrothiolation of 1,3-dienes was discovered by changing the solvent. The origin of the observed selectivity was explained through density functional theory calculations.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Jun Zheng, Ali Nikbakht, Bernhard Breit
Summary: A dual palladium/photoredox-catalyzed regio- and enantioselective decarboxylative hydroaminoalkylation of allenes with amino acids was reported. This method allows efficient access to protected vinyl 1,2-amino ethers with high levels of branched and enantioselectivity.
Article
Chemistry, Applied
Yunhe Lv, Jinhui Xie, Weiya Pu, Xue Wang, Huanhuan Zhang, Xuerui Li, Yan Liu, Fei Chen, Yunfeng Xu
Summary: We developed a strategy for the copper-catalyzed three-component reaction to synthesize tetrasubstituted allenes with phosphinoyl and cyano groups. The reaction exhibited high functional group compatibility and good yields under mild conditions. A preliminary reaction mechanism involving the formation of phosphinoyl radicals and their regioselective addition to 1,3-enynes was proposed.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Guolin Wu, Yuan Yao, Gen Li, Xue Zhang, Hui Qian, Shengming Ma
Summary: This study developed a catalytic recipe of copper halides to address the issues of side reactions and selectivity in the 1,5-H transfer of alka-1,4-diyn-3-yl amines, providing various allenynes with excellent enantioselectivities. The method was successfully applied to the first highly enantioselective total synthesis of the natural product scorodonin. Mechanistic studies and DFT calculations elucidated the regioselectivity for the observed 1,5-H transfer.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Wei Tang, Chuan Wang
Summary: Here we report a new method for the regioselective reductive aminolysis of nitroarenes to synthesize amino diols with high diastereofidelity. This step-economical process utilizes the dual function of bis-boric acid, acting as a reductant for the reduction of nitro compounds and promoting the ring opening reaction of 3,4-epoxy alcohols with in situ-generated anilines.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Manuel Plaza, Johannes Grosskopf, Stefan Breitenlechner, Christoph Bannwarth, Thorsten Bach
Summary: The research investigated the photochemical deracemization of 2,4-disubstituted 2,3-butadienamides using experimental and theoretical approaches. A chiral sensitizer was found to catalyze the reaction, leading to the isolation of enantioenriched allene amides with high yield. The study revealed the binding properties and selectivity differences between the two enantiomers through luminescence data, DFT calculations, and NMR titration.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Ke-Qin Wu, Hui Li, Ao Zhou, Wei-Ran Yang, Qin Yin
Summary: A Pd-catalyzed regioselective C-H bond allylic alkylation of phenols with 1,3-dienes is reported, which selectively functionalizes the ortho C-H bond of 2-naphthols, 1-naphthols, and electron-rich phenols to synthesize phenol derivatives with diverse structures. The reaction is accelerated by a diphosphine ligand, does not require any other additive, and exhibits broad substrate scope and good chemo- and regioselectivity. Additionally, an asymmetric variant is investigated, achieving product with up to 55% enantiomeric excess.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Amritha Rayaroth, Afna Elikkottil, Chithra Mohan Jayakumari, Kalyanakrishnan Arayil Vennoli, Sivaranjana Reddy Vennapusa, Alagiri Kaliyamoorthy
Summary: We have developed a method for regioselective allenylation and propargylation using unfunctionalized 2-alkynyl azaarenes as pronucleophiles with the appropriate choice of base. The reaction can be directed towards either the formation of allenylated or propargylated products using different bases. Additionally, this strategy is scalable and can be performed on a gram scale.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Medicinal
Siyuan Wu, Shinji Harada, Takahiro Morikawa, Atsushi Nishida
CHEMICAL & PHARMACEUTICAL BULLETIN
(2018)
Article
Chemistry, Organic
Shigeru Arai, Koki Matsumoto, Atsushi Nishida
Article
Chemistry, Organic
Shigeru Arai, Koichi Nakazawa, Xiao-fei Yang, Atsushi Nishida
Review
Chemistry, Medicinal
Shigeru Arai
CHEMICAL & PHARMACEUTICAL BULLETIN
(2019)
Review
Chemistry, Organic
Shigeru Arai, Yuka Amako, Hiroto Hori, Atsushi Nishida
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2019)
Article
Chemistry, Applied
Shigeru Arai, Arisa Izaki, Yuka Amako, Masaya Nakajima, Masanobu Uchiyama, Atsushi Nishida
ADVANCED SYNTHESIS & CATALYSIS
(2019)
Article
Chemistry, Organic
Shigeru Arai, Yuna Kawata, Yuka Amako, Atsushi Nishida
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Multidisciplinary
Shinji Harada, Saki Nakashima, Shihori Sekino, Wakana Oishi, Atsushi Nishida
CHEMISTRY-AN ASIAN JOURNAL
(2020)
Article
Chemistry, Organic
Shigeru Arai, Yuichi Sato, Natsuki Ito, Atsushi Nishida
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Organic
Yuna Kawata, Shigeru Arai, Masaya Nakajima, Atsushi Nishida
Summary: The highly regio- and stereoselective homodimerizative [2 + 2] cycloaddition of allenamides under nickel catalysis was investigated, with Xantphos ligand playing a crucial role in product formation. DFT studies revealed that oxidative addition is a key process, leading to the formation of cyclobutane as a single isomer in a sequential manner.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Shigeru Arai, Saki Inagaki, Masaya Nakajima, Atsushi Nishida
Summary: Vinylallenes have been recognized as versatile C2 and C4 components for nickel-catalyzed intramolecular [4+2] and [2+2] cycloadditions, with up to 90% yield for the former and up to 88% yield for the latter. DFT studies revealed a concerted mechanism involving the activation of different C-C multiple bonds in the substrates for both reaction pathways.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Hiroto Hori, Shigeru Arai, Atsushi Nishida
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
