Article
Chemistry, Organic
Takashi Mino, Kaho Takaya, Kaito Koki, Natsume Akimoto, Yasushi Yoshida, Yoshio Kasashima, Masami Sakamoto
Summary: We synthesized N-alkyl-N-cinnamoyl amide type phosphine-olefin compounds 1 and observed axial chirality in the C(aryl)-N(amide) bond of compounds 1 using HPLC analysis with a chiral stationary phase column. Enantiomeric isomers of 1 were obtained and (-)-1 was demonstrated as a chiral ligand in Pd-catalyzed asymmetric allylic substitution reactions, leading to high enantioselectivity (up to 97% ee) in the esterification process.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Jie Zhang, Yaning Wang, Chang You, Mingying Shi, Xueling Mi, Sanzhong Luo
Summary: We report a synergetic chiral primary amine and rhodium catalysis for the asymmetric coupling of beta-ketocarbonyls and alkynes. This method enables the synthesis of linear allylation products with all-carbon quaternary centers in high regio- and enantioselectivities.
Article
Chemistry, Organic
Xiuju Cai, Xiaoyu Zhou, Ming Huang
Summary: Selective mono-N-methylation of amines with methanol remains challenging, especially for aliphatic amines. In this study, a series of N-heterocyclic carbene (NHC)-amine Ru complexes were developed for this transformation. The Ru4 complex with an NHC-aniline ligand displayed the highest activity and excellent tolerance towards various substrates and sensitive groups.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Qianqian Zhang, Yifan Sun, Wei Li, Jinli Zhang, Yan Fu
Summary: In this study, Pd/SnO2 nanocatalysts were synthesized and used for selective hydrogenation of a, b-unsaturated aldehydes. The results showed high selectivity and faradaic efficiency, outperforming commercial Pd/C catalysts.
INTERNATIONAL JOURNAL OF HYDROGEN ENERGY
(2022)
Article
Chemistry, Multidisciplinary
Xiao-Bing Lan, Zongren Ye, Chenhui Yang, Weikang Li, Jiahao Liu, Ming Huang, Yan Liu, Zhuofeng Ke
Summary: This study presents a tungsten-catalyzed N-alkylation reaction using primary alcohols with anilines via BH/HA, demonstrating the tolerance of various functional groups, including challenging substrates with sterically hindered substituents or heteroatoms. Mechanistic insights based on experimental and computational studies are provided.
Article
Chemistry, Organic
Hua-Dong He, Zhi-Kai Zhang, Hao-Bo Tang, Yuan-Qing Xu, Xiao-Bo Xu, Zhong-Yan Cao, Hao Xu, Yang Li
Summary: A practical method for the synthesis of N,N-dialkyl anilines via reductive dialkylation has been developed using inexpensive substrates and cheap NiI2 as the key promoter. This method demonstrates high functional group tolerance and can be used for the synthesis and modification of drugs or pesticides.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Physical
Weikang Li, Ming Huang, Jiahao Liu, Yong-Liang Huang, Xiao-Bing Lan, Zongren Ye, Cunyuan Zhao, Yan Liu, Zhuofeng Ke
Summary: This study demonstrates the effective N-alkylation of anilines or challenging nitroarenes with alcohols through homogeneous Mo-catalysis, utilizing a strong hydride-donating ability of the easily accessible bis-NHC-Mo(0) complex. The enhanced hydride-donating strategy is valuable for designing highly active systems for borrowing hydrogen transformations.
Article
Chemistry, Organic
Charlotte E. Coomber, Louis J. Diorazio
Summary: The iridium catalysed N-alkylation of alpha-amino esters and amides using alcohols through hydrogen borrowing method has been developed. This protocol is applicable to both free base and hydrochloride salts of the amines and produces water as the sole by-product. This transformation provides an easy access to chiral N-alkyl amines from readily available starting materials in a simple one-step reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zhenzhong Zhang, Takuya Ikeda, Haruno Murayama, Tetsuo Honma, Makoto Tokunaga, Yukihiro Motoyama
Summary: Carbon-nitrogen bond formation is crucial for the production of valuable chemicals. This study presents a novel palladium catalyst that selectively hydrogenates imines while leaving other carbonyl groups intact. This catalyst allows for efficient synthesis of functionalized secondary amines under mild conditions.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
Ruiqin Zhang, Yuxin Ding, Renchao Ma, Xuqiong Xiao, Rener Chen, Lei Wang, Yongmin Ma
Summary: An efficient synthesis method for multi-substituted pyridines and pyrroles from aryl methyl ketones with 1-amino-2-methylpropan-2-ol and 1,2-diamino-2-methylpropane has been developed. The reactions involve cleavage of a C-N bond and formation of two new bonds (C-C bond and C-N bond) through an oxidative cyclization process promoted by I-2/PhNO2. The selective cleavage occurs at the C-N bond adjacent to the primary carbon of 1,2-diamino-2-methylpropane.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Luxia Guo, Jiaqi Li, Luigi Vaccaro, Minghao Li, Yanlong Gu
Summary: A direct synthesis method catalyzed by kalinite has been developed for the efficient preparation of N-substituted 3-carbonylpyrroles, with potential applications in biological and material fields.
Article
Chemistry, Multidisciplinary
Hongfa Wang, Ruiyuan Zhang, Qinglong Zhang, Weiwei Zi
Summary: A new method for metal-hydride-catalyzed hydroalkylation of 1,3-dienes with aldehydes is described, providing access to chiral molecules with allylic stereocenters. By choosing a combination of chiral palladium and amine catalysts, highly diastereo- and enantioselective access to complementary diastereomers is achieved. The mechanism involves PdH formation and migratory insertion into the alkene, followed by C-C bond formation, with the origin of stereoselectivities investigated through distortion/interaction analysis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Xin-Yang Lv, Ruben Martin
Summary: Here, the development of a copper-catalyzed C-(sp(3)) amination of unactivated secondary alkyl iodides mediated by diaryliodonium salts is described. The method involves the intermediacy of aryl radical species that undergo halogen atom transfer prior to interfacing with copper catalysts, enabling the formation of C-N bonds at sp(3)-hybridized carbons. The protocol is characterized by its mild reaction conditions, excellent regioselectivity, and wide substrate scope.
Article
Chemistry, Organic
Nicholas A. Clanton, Taylor E. Spiller, Eliezer Ortiz, Zhinong Gao, Juan Manuel Rodriguez-Poirier, Albert J. DelMonte, Doug E. Frantz
Summary: A metal-free method has been developed for the reductive N-alkylation of indoles using aldehydes and inexpensive Et3SiH as the reductant. A wide range of aromatic and aliphatic aldehydes, as well as various substituted indoles, are viable substrates. The method was successfully demonstrated on a 100 mmol scale for a one-pot sequential 1, 3-alkylation of a substituted indole.
Article
Chemistry, Organic
Yue Weng, Bo Ding, Yunqing Liu, Chunlan Song, Lo-Ying Chan, Chien-Wei Chiang
Summary: This study presents a novel visible-light-induced late-stage photoredox C-H amidation method for the modification of N-unprotected indoles and tryptophan-containing peptides, leading to the formation of N-(indol-2-yl)amide derivatives. The mechanism involves the oxidative C-H functionalization of indole with a PS* to PS center dot- cycle, providing a new toolkit for the late-stage modification labeling and peptide-drug conjugation of N-unprotected indole derivatives.
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)
