Article
Chemistry, Organic
Yifei Qu, Xiaojia Cai, Yuzhuang Guan, Jiamin Tan, Zhangping Cai, Minyun Liu, Yasi Huang, Jinhui Hu, Wen-Hua Chen, Jia-Qiang Wu
Summary: A facile and straightforward method for the successful synthesis of difluoromethylated indole-3-carbinols, bisindolylmethanes, and indole-3-methanamines by a Friedel-Crafts reaction is developed, showing good to excellent yields, broad substrate compatibility, good functional group tolerance, and scalability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Xi Xiao, Xiaobiao Lu, Ming Zhang, Haoqing Hou, Changfeng Wan, Jinbiao Liu
Summary: A novel synthetic method was successfully developed for the preparation of multisubstituted dihydrochromeno[2,3-b]indole derivatives in moderate to high yields using a catalytic environmentally benign iron salt.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jinming Zheng, Qingzong Wang, Yifei Li, Huixian Zheng, Chaoyi Hu, Xiaodong Hu, Xiaoxia Ye, Jiuxi Chen, Renhao Li
Summary: A direct access to substituted dihydrochalcones from easily available starting materials 3-hydroxypropionitrile derivatives and arylboronic acids is described. The procedure involves a multicomponent aryl addition/hydroxylelimination/reduction Heck approach using a Pd catalyst with excellent functional group tolerance and a wide range of substrates. In addition, the mixed 1,3-diarylation of 3-hydroxypropanenitrile using two arylboronic acids with different electronic properties was also achieved.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xian-Tao Wu, Feng Ma, En-Kai Xiao, Jin Yin, Fuxing Sun, Qiang Wang, Yi-Jun Jiang, Peng Chen
Summary: A simple and efficient methodology for the first synthesis of tri- and di-fluoromethyl-bis(indolyl)methanols has been demonstrated through a one-pot Friedel-Crafts-type acylation-alkylation of readily available indoles and fluorinated acids. This method was performed under metal-, additive-, toxic-solvent-, and protective-gas-free conditions, delivering a wide range of products in moderate to high yields. The reaction can tolerate diverse functional groups and can be readily scaled up without significant decrease in yield, showing its high application potential.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Chao Gao, Jian Xu, Shuxian Zhu, Kaixia Jian, Qingqing Xuan, Qiuling Song
Summary: The study demonstrates that under appropriate conditions, 3-(2-azidoaryl) substituted propargyl alcohols can undergo chemoselective oxidative radical cyclizations to form a series of anthranils, with the reaction triggered mainly by the direct attack of oxygen radicals on azides.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Bo-Sheng Zhang, Fan Wang, Xue-Ya Gou, Ying-Hui Yang, Wan-Yuan Jia, Yong-Min Liang, Xi-Cun Wang, Yuke Li, Zheng-Jun Quan
Summary: In the Catallani-Lautens reaction system, a highly selective C-N coupling reaction was achieved by recovering the ortho effect, leading to a one-step synthesis of highly functionalized tricyclic indole derivatives.
Article
Chemistry, Organic
Takashi Mino, Toshiki Yamaoka, Kohei Watanabe, Chihiro Masuda, Shohei Kasano, Yasushi Yoshida, Ryo Takita, Yoshio Kasashima, Masami Sakamoto
Summary: P,olefin ligand/palladium catalyst systems can easily afford the corresponding 2-substituted 3-allylindole derivatives in good to excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Mingqin Zhao, Xinyan Li, Xiaoyu Zhang, Zhihui Shao
Summary: The catalytic dehydrogenation of alcohols is crucial for sustainable production of valuable products, providing a new strategy for green organic synthesis in chemical industries. This study introduces a manganese-based catalytic system that efficiently synthesizes C3-alkylated indoles from benzyl alcohols and indoles via the borrowing hydrogen process. Furthermore, dehydrogenative coupling of 2-arylethanols and indoles yields C3-alkenylated indoles. Additionally, reacting 2-aminophenethanol instead of indoles under the same conditions also yields the corresponding indole products with high selectivity.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Feng Jiang, Feng Zhao, Youliang He, Xiantao Luo, Xiaoming Wang
Summary: A new method combining iridium catalysis and photochemical organocatalysis has been developed to convert amides into beta-substituted tertiary alkylamines, with high yields and a wide substrate scope.
CELL REPORTS PHYSICAL SCIENCE
(2022)
Article
Chemistry, Multidisciplinary
Feng Jiang, Feng Zhao, Youliang He, Xiantao Luo, Xiaoming Wang
Summary: In this study, a combination of iridium catalysis and photochemical organocatalysis was developed for the deoxygenative conversion of amides to beta-substituted tertiary alkylamines with moderate to excellent yields (up to 93%) and broad substrate scope (57 examples).Mechanistic studies suggest that the interaction of iridium-catalyzed partial reduction of amides and photochemical organocatalysis of alpha-bromoketones under visible light is crucial for this cross-coupling process. The active electrophilic radicals from photochemical organocatalysis act as functionalization partners with the in-situ-formed enamine intermediates from the Ir-catalyzed reduction of amides, leading to the formation of beta-substituted amines.
CELL REPORTS PHYSICAL SCIENCE
(2022)
Article
Chemistry, Multidisciplinary
Matthias Elfinger, Timon Schoenauer, Sabrina L. J. Thomae, Robert Staeglich, Markus Drechsler, Mirijam Zobel, Juergen Senker, Rhett Kempe
Summary: The 3D metal catalyst developed here utilizes hydrogen as the reducing agent and easily handled ammonia dissolved in water as the nitrogen source for the synthesis of primary amines. The catalyst operates under mild conditions and outperforms commercially available noble metal catalysts. The key to its high activity is the unique support material it uses.
Article
Chemistry, Organic
Chandrahas Tarigopula, Seetharaman Manojveer, Rengarajan Balamurugan
Summary: A novel method is proposed for constructing benzene rings using propargylic alcohols and 1,3-dicarbonyls, involving multiple C-C bond formations to obtain substituted biaryls. The unique reactivity of an acetal formed under the reaction conditions is harnessed in this Bronsted acid-promoted protocol, allowing for the use of alkynyl methyl ketones as a substitute for 1,3-dicarbonyls.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Marianna Kocsis, Kornelia Baan, Sandor B. Otvos, Akos Kukovecz, Zoltan Konya, Pal Sipos, Istvan Palinko, Gabor Varga
Summary: Oxidative dehydrogenative coupling (ODC) is a versatile and sustainable tool for forming new C-C, C-O, and N=N bonds. However, it is less explored for N-heterocycle synthesis. In this study, we developed an environmentally friendly synthesis strategy to selectively produce azobenzenes, quinolines, and quinoxalines through the ODC of anilines and 2-aminoanilies with vicinal diols. The reactions were catalyzed by bifunctional catalysts based on transition metal oxides/Bi(iii), enabling solvent-, additive-, oxidant-, and base-free cyclizations/couplings. The catalysts showed high robustness and reusability.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Organic
Leonardo Straminelli, Francesco Vicentini, Antonio Di Sabato, Carmela Maria Montone, Chiara Cavaliere, Kari Rissanen, Francesca Leonelli, Fabrizio Vetica
Summary: A highly stereoselective procedure for the synthesis of spiro-polycyclic oxindoles bearing five contiguous stereogenic centers including two tetrasubstituted carbons has been developed. The sequence involves sequential organocatalysis using a pyrrolidine-based organocatalyst and DBU, resulting in an atom-economical Michael-domino Michael/aldol reaction sequence. The reaction yielded variously functionalized spiro-decalin oxindoles with excellent stereoselectivity (>99:1 dr, up to 92% ee).
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Qiwen Gao, Jinhong Tian, Kangmei Wen, Chen Chen, Xingang Yao, Jianxin Pang, Xiaodong Tang
Summary: In this study, a copper-mediated C4-benzylation reaction of 5-aminopyrazoles with 3-indoleacetic acids was presented. Various benzylated 5-aminopyrazoles were synthesized in good-to-excellent yields under basic and ligand-free conditions in the presence of copper acetate. The benzylation method was also applied to other substrates and showed potential antiproliferative activities against cancer cell lines. Moreover, the C4-benzylated products underwent cyclization with aldehydes to form 1H-pyrazolo-[4 ',3 ':6,7]-azepino-[3,4-b]-indoles via one-pot two-step processes. The cyclized products exhibited fluorescence emissions with large Stokes shifts.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
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)
