Article
Chemistry, Organic
Lin Li, Xin-Lian Liu, Zhuang Qi, Ai-Hua Yang, Ai-Jun Ma, Jin-Bao Peng
Summary: A palladium-catalyzed carbonylative Sonogashira/annulation reaction has been developed for the synthesis of indolo[1,2-b]isoquinolines, which establishes three C-C bonds and a C-N bond in one step.
Article
Chemistry, Organic
Chaoyi Wu, Jin Lin, Xu Tian
Summary: An efficient Mizoroki-Heck/amination cascade reaction of o-dihaloarenes with cyclic imines was achieved using nickel and a sterically bulky N-heterocyclic carbene ligand. This method provides a straightforward synthesis of a variety of indole[2,1-a]isoquinolines from readily available starting materials. The cascade approach is applicable for the synthesis of the natural product cryptowoline.
Article
Chemistry, Multidisciplinary
Dong Gao, Lei Jiao
Summary: This study presents an efficient method for constructing indoline structures with a C2-quaternary stereocenter and controlling the migrating group through aza-semipinacol rearrangement. It enables the divergent access to dearomatized indole derivatives with either a C3- or a C2-quaternary stereocenter.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Oliver R. Gedde, Andreas Bonde, Peter Golbaekdal, Troels Skrydstrup
Summary: An expedient method for the ex-situ generation of difluoroiodomethane (DFIM) and its immediate use in a Pd-catalyzed difluoromethylation reaction is reported. The method involves heating a solution of bromodifluoroacetic acid with sodium iodide in sulfolane to generate near stoichiometric amounts of DFIM, which is then used for the subsequent catalytic coupling step. The method allows for the installation of fluorine-containing C-1 groups onto pharmaceutically relevant molecules and is adaptable for deuterium incorporation by adding D2O to the DFIM-generating chamber.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Shunsuke Watanabe, Yuki Wada, Masaki Kawano, Shuhei Higashibayashi, Takeshi Sugai, Kengo Hanaya
Summary: This study demonstrates a method for C-N coupling of tryptophan with azoles using an in situ-generated iodine-based oxidant. It allows selective modification of tryptophan in nonprotected polypeptides bearing oxidatively sensitive residues. This method enables the attachment of reactive handles to polypeptides and peptide stapling.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Wei Tian, Bowen Li, Duanshuai Tian, Wenjun Tang
Summary: A palladium-catalyzed 2-alkylation of indoles with alpha-bromo esters using a P,P=O ligand has been developed. The method shows excellent regioselectivities, mild reaction conditions, and good functional group compatibility. Mechanistic studies indicate that the reaction proceeds through a radical pathway.
CHINESE CHEMICAL LETTERS
(2022)
Review
Biochemistry & Molecular Biology
Liangxin Fan, Xinxin Zhu, Xingyuan Liu, Fangyu He, Guoyu Yang, Cuilian Xu, Xifa Yang
Summary: This review summarizes recent developments in the synthesis of these tricyclic indoles with palladium-catalyzed domino reactions and their applications in the total synthesis of representative natural products.
Article
Chemistry, Multidisciplinary
Peng Zhang, Qi Xu, Xiao-Mei Wang, Jia Feng, Chuan-Jun Lu, Yingzi Li, Ren-Rong Liu
Summary: The first enantioselective synthesis of N-N bisindole atropisomers via palladium-catalyzed construction of one indole skeleton is reported in this study. A wide variety of N-N axially chiral bisindoles were generated with good yields and excellent enantioselectivities through a cascade condensation/N-arylation reaction. The reaction mechanism and enantiocontrol were further investigated using density functional theory (DFT) calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Wangqin Ji, Hai-Hong Wu, Wenbo Li, Junliang Zhang
Summary: A novel, simple, effective, and rapid synthetic method has been developed for constructing C-2 trifluoromethylated indolinyl ketones via a copper-catalyzed cyclization reaction. The reaction likely involves a radical mechanism through a single-electron transfer process, with broad substrate scope, good functional groups, high diastereoselectivities (up to >20:1), and gram-scale synthesis, making this approach highly attractive.
CHEMICAL COMMUNICATIONS
(2021)
Article
Multidisciplinary Sciences
Igor Beckers, Dirk De Vos
Summary: In this work, the turnover rate of a Pd-catalyzed C-H arylation reaction was maximized through rational tuning of the ligands. A kinetic model was derived from a computational study and used to explain the experimental time profiles. The study also revealed quantitative structure-activity relationships between the ligand substituents and catalytic activity for different C-H arylations.
Article
Chemistry, Multidisciplinary
Xiaolin Shi, Zemin Wang, Yuxiu Li, Xiaowei Li, Xiangqian Li, Dayong Shi
Summary: The study reports a challenging palladium-catalyzed remote C4-H phosphonylation of indoles using a radical approach. The method not only provides a new synthetic pathway, but also unexpectedly obtained C6-phosphonylated indoles, suggesting a potential strategy for future cross-coupling reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Xiang Huang, Xing Chen, Haisheng Xie, Zheng Tan, Huanfeng Jiang, Wei Zeng
Summary: A photocatalyzed in situ denitrogenative sulfonylation of N-arylsulfonyl hydrazones has been developed, providing a low-carbon strategy to assemble arylalkyl sulfones in a stepwise denitrogenation/sulfonylation manner.
Article
Chemistry, Organic
Takashi Mino, Yohei Fujisawa, Shizuki Yoshida, Mitsuru Hirama, Takumu Akiyama, Ryo Saito, Yasushi Yoshida, Yoshio Kasashima, Masami Sakamoto
Summary: By synthesizing cinnamoyl amide type chiral P,olefin ligand (S)-4, separable diastereomers of 4d were obtained successfully, and asymmetric allylic substitution reactions of indoles using (S,aS)-4d as a chiral ligand demonstrated high enantioselectivities (up to 98% ee).
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Antonio Arcadi, Andrea Calcaterra, Marco Chiarini, Giancarlo Fabrizi, Andrea Fochetti, Antonella Goggiamani, Antonia Iazzetti, Federico Marrone, Vincenzo Marsicano, Andrea Serraiocco
Summary: The palladium-catalyzed synthesis of indole/benzofuran-containing diarylmethanes was investigated, showing that the choice of precatalyst is crucial for the success of the reaction. Different precatalysts were found to be more efficient for different substrates, leading to good to high yields. This methodology can be extended to the preparation of a key precursor of Zafirlukast.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Applied
Su Chen, Monica Oliva, Luc Van Meervelt, Erik V. Van der Eycken, Upendra K. Sharma
Summary: The study presents a palladium-catalyzed cascade reaction to construct difunctionalized acyl indoles, involving multiple bond formations in a single operational step. Enantioselectivity at a quaternary carbon center is attempted. Additionally, a continuous-flow process is demonstrated for the synthesis of aryl isocyanides within minutes and their telescopic use.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
