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Chemistry, Organic
Ninghui Zhang, Chunli Zhang, Xiaoping Hu, Xin Xie, Yuanhong Liu
Summary: An efficient nickel-catalyzed addition of benzyl nitriles to terminal vinyl ketones via C(sp(3))-H functionalization has been developed, providing a novel protocol for the synthesis of α-functionalized benzyl nitriles with structural diversity under mild reaction conditions without the use of a strong base. This work might be potentially useful towards the development of an enantioselective variant using chiral nitrogen ligands.
Editorial Material
Chemistry, Organic
Kazuhiko Semba, Kotaro Nagase, Yoshiaki Nakao
Summary: The catalytic activity of nickelacycles in the conjugate addition of arylboronates to alpha,beta-unsaturated ketones was investigated. Nickelacycles were found to catalyze the reaction effectively, while an analogous palladacycle did not show any catalytic activity.
Article
Chemistry, Organic
Feng Chen, Xiu-Hua Xu, Feng-Ling Qing
Summary: This study presents a direct and efficient method for the synthesis of 1-bromo-1-fluoroalkanes from unactivated alkenes and dibromofluoromethane under photoredox catalysis. The key to the success of these reactions lies in the appropriate choice of photoredox catalyst. The prepared 1-bromo-1-fluoroalkanes can be further transformed into various fluorine-containing compounds.
Article
Chemistry, Multidisciplinary
Zhi-Peng Bao, Youcan Zhang, Xiao-Feng Wu
Summary: The introduction of fluorine atoms into organic molecules is an attractive topic. This work developed an interesting palladium-catalyzed reaction to transform aryl olefins into difluoropentanedioate compounds with good functional-group tolerance and high regioselectivity. Ethyl bromodifluoroacetate acts as both a difluoroalkyl precursor and a nucleophile in this reaction. Additionally, successful scale-up reactions and further transformations of the obtained product were demonstrated.
Article
Chemistry, Organic
Benat Lorea, Ane Garcia-Urricelqui, Josee M. Odriozola, Jesus Razkin, Maialen Espinal-Viguri, Mikel Oiarbide, Antonia Mielgo, Jesus M. Garcia, Claudio Palomo
Summary: The direct asymmetric conjugate addition of unactivated α-branched nitroalkanes can be achieved using chiral amine/ureidoaminal bifunctional catalysts and a tunable acrylate template, resulting in tertiary nitrocompounds with high enantioselectivity. Elaboration of the ketol moiety allows for the preparation of various derivatives, including carboxylic acids, aldehydes, nitriles, and enantioenriched 5,5-disubstituted γ-lactams.
Article
Chemistry, Applied
Qingyu Yin, Zhiming Li, Fan Wu, Mingtong Ji, Chao Fu, Xiaoyu Wu
Summary: A diastereoselective and enantioselective conjugate addition of alpha-substituted acyl imidazole to nitroalkene catalyzed by nickel bisoxazoline complex and B(C6F5)(3) has been developed. The reaction showed broad substrate tolerance and high yields and enantioselectivity. The coordination catalyst and co-catalyst played a crucial role in the success of the reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Jianrong Steve Zhou, Xiaolei Huang, Shenghan Teng, Yonggui Robin Chi
Summary: Nickel-catalyzed Heck reaction of cycloalkenes produces unusual conjugated arylated isomers. The omission of bases allows nickel hydride species to perform in situ olefin isomerization of initial Heck adducts, enhancing the reactivity of aryl triflates, mesylates, tosylates, and pivalates.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Kentaro Yamakawa, Kana Sakamoto, Takahiro Nishimura
Summary: The enantioselective addition of an imide N-H bond to alkenes has been achieved using a cationic iridium catalyst. Bulky diphosphine ligands were crucial for the reaction, and various substrates including styrene derivatives, allylsilanes, and norbornene gave chiral adducts with high enantioselectivity.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Kentaro Yamakawa, Kana Sakamoto, Takahiro Nishimura
Summary: In this study, enantioselective addition of an imide N-H bond to alkenes was achieved using a cationic iridium catalyst. Bulky diphosphine ligands played a crucial role in the reaction. Various substrates, such as styrene derivatives, allylsilanes, and norbornene, reacted well with alkenes to afford chiral adducts with high enantioselectivity.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Jin Cui, Sadhanendu Samanta, Takumi Watanabe, Masakatsu Shibasaki
Summary: In this report, the efficient synthesis of interesting molecules through direct 1,6-conjugate addition of butenolide to p-quinone methides via Bronsted base catalysis is presented. The reaction exhibits regioselective gamma-attack of butenolide and demonstrates good functional group tolerance.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiaoxue Wu, Yanhao Su, Guofu Zi, Weiping Ye, Guohua Hou
Summary: The asymmetric hydrogenation of a-substituted alkenyl sulfones using Rh-(R,R)-f-spiroPhos complex catalyst has been successfully achieved, resulting in high yields (96-99%) of chiral ?-keto sulfones and simple a-alkyl-substituted sulfones with excellent chemo-/enantioselectivities (86-96% ee) and high turnover numbers (TONs) of up to 4000. This method provides an efficient and high-enantioselectivity strategy for the synthesis of chiral ?-keto sulfones and simple a-substituted sulfones under mild conditions. Additionally, the obtained hydrogenation product can be transformed into other important chiral a-substituted sulfones.
Article
Chemistry, Organic
Qiuling Song, Fumei Ke, Changjiang Yu, Xin Li, Heyun Sheng
Summary: A convenient method for synthesizing fluorine-containing heterocyclic compounds was developed, involving copper-catalyzed free radical addition and molecular lactone exchange of alkynol and ethyl bromodifluoroacetate. This method offers easy availability of raw materials, good stereochemical selectivity, and simple operation. It also allows for the synthesis of valuable tetrasubstituted E-configurated alkenes and various vinyl C-Br bonds and difluoromethylene-containing functionalized heterocycles.
Article
Chemistry, Multidisciplinary
Daisuke Yamauchi, Ikumi Nakamura, Takahiro Nishimura
Summary: The Ir-catalyzed enantioselective addition of an N-methyl C-H bond of 2-(methylamino)pyridine derivatives to alpha-trifluoromethylstyrenes proceeded via C-H activation to give chiral gamma-branched amine derivatives having a trifluoromethyl-substituted stereocenter. It was found that a bulky and electron-withdrawing group at the 3-position of 2-(methylamino)pyridines was necessary for the present C-H addition reaction catalyzed by a cationic iridium/chiral bisphosphine complex.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Applied
Anil Kumar Khatana, Vikram Singh, Manoj Kumar Gupta, Bhoopendra Tiwari
Summary: A novel method for the synthesis of 3,6-disubstituted alpha-pyrones via Michael addition/lactonization/elimination cascade reactions is reported in this study, showing promising research and application prospects.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Jinyi Qian, Hengyuan Zhao, Qi Gao, Lirong Chen, Yinrui Shi, Jiuling Li, Yafei Guo, Baomin Fan
Summary: In this research, a new strategy for the asymmetric carbon-phosphorus bond forming reaction using CBS catalysts via non-covalent interactions was disclosed. Various alpha,beta-unsaturated ketones showed remarkable tolerance to various diarylphosphine oxides, and a new application of oxazaborolidines in enantioselective phospha-Michael addition to alpha,beta-unsaturated ketones under mild reaction conditions was developed.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Eiichi Kayahara, Toshiki Hayashi, Katsuhiko Takeuchi, Fumiyuki Ozawa, Keita Ashida, Sensuke Ogoshi, Shigeru Yamago
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Masato Ohashi, Naoyoshi Ishida, Kota Ando, Yu Hashimoto, Anna Shigaki, Kotaro Kikushima, Sensuke Ogoshi
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Multidisciplinary
Yoichi Hoshimoto, Takuya Kinoshita, Sunit Hazra, Masato Ohashi, Sensuke Ogoshi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Chemistry, Multidisciplinary
Takuya Kinoshita, Mahiro Sakuraba, Yoichi Hoshimoto, Sensuke Ogoshi
Article
Chemistry, Organic
Hiroshi Shirataki, Masato Ohashi, Sensuke Ogoshi
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Takuya Kawashima, Masato Ohashi, Sensuke Ogoshi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Chemistry, Organic
Hiroshi Shirataki, Takafumi Ono, Masato Ohashi, Sensuke Ogoshi
Article
Chemistry, Multidisciplinary
Hironobu Sakaguchi, Masato Ohashi, Sensuke Ogoshi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Masato Ohashi, Takuya Adachi, Naoyoshi Ishida, Kotaro Kikushima, Sensuke Ogoshi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Multidisciplinary
Yoichi Hoshimoto, Takahiro Asada, Sunit Hazra, Masato Ohashi, Sensuke Ogoshi
Article
Chemistry, Multidisciplinary
Yukari Hayashi, Yoichi Hoshimoto, Ravindra Kumar, Masato Ohashi, Sensuke Ogoshi
Article
Chemistry, Multidisciplinary
Yoichi Hoshimoto, Keita Ashida, Yukari Sasaoka, Ravindra Kumar, Ken Kamikawa, Xavier Verdaguer, Antoni Riera, Masato Ohashi, Sensuke Ogoshi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Multidisciplinary
W. Tao, S. Akita, R. Nakano, S. Ito, Y. Hoshimoto, S. Ogoshi, K. Nozaki
CHEMICAL COMMUNICATIONS
(2017)
Article
Chemistry, Multidisciplinary
Yoichi Hoshimoto, Yukari Hayashi, Masato Ohashi, Sensuke Ogoshi
CHEMISTRY-AN ASIAN JOURNAL
(2017)
Article
Chemistry, Multidisciplinary
Masato Ohashi, Yuta Ueda, Sensuke Ogoshi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
