1132765-72-0Relevant articles and documents
Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts
No?l, Timothy,Sambiagio, Carlo,Sch?nbauer, David,Schnürch, Michael
, p. 809 - 817 (2020)
A ruthenium-catalyzed photoredox coupling of substituted N-aryltetrahydroisoquinolines (THIQs) and different bench-stable pyridinium salts was successfully developed to give fast access to 1-benzyl-THIQs. Furthermore, secondary alkyl and allyl groups were also successfully introduced via the same method. Additionally, the typically applied N-phenyl group in the THIQ substrate could be replaced by the cleavable p-methoxyphenyl (PMP) group and successful N-deprotection was demonstrated.
Synthesis of Dihydroindoloisoquinolines through Copper-Catalyzed Cross-Dehydrogenative Coupling of Tetrahydroisoquinolines and Nitroalkanes
Martín-García, Iris,Alonso, Francisco
, p. 18857 - 18862 (2018)
Lately, the cross-dehydrogenative coupling of tetrahydroisoquinolines and nitroalkanes has become a widely studied reaction in organic chemistry; the corresponding β-nitroamines are generally formed irrespective of the catalysis and activation mode utiliz
Direct Near Infrared Light–Activatable Phthalocyanine Catalysts
Katsurayama, Yoshino,Ikabata, Yasuhiro,Maeda, Hajime,Segi, Masahito,Nakai, Hiromi,Furuyama, Taniyuki
supporting information, (2021/12/22)
The high penetration of near-infrared (NIR) light makes it effective for use in selective reactions under light-shielded conditions, such as in sealed reactors and deep tissues. Herein, we report the development of phthalocyanine catalysts directly activa
A Short Approach to N -Aryl-1,2,3,4-tetrahydroisoquinolines from N -(2-Bromobenzyl)anilines via a Reductive Amination/Palladium-Catalyzed Ethoxyvinylation/Reductive N -Alkylation Sequence
Glas, Carina,Wirawan, Ricky,Bracher, Franz
, p. 1943 - 1954 (2021/01/18)
N -Aryl-1,2,3,4-tetrahydroisoquinolines are obtained via a convenient and short protocol with a broad range of substituents on both aromatic rings and high functional group tolerance. Starting from readily available ortho -brominated aromatic aldehydes and primary aromatic amines, condensation of these building blocks under reductive conditions gives N -aryl 2-bromobenzylamines. The C-3/C-4-unit of the tetrahydroisoquinoline is introduced using commercially available 2-ethoxyvinyl pinacolboronate under Suzuki conditions. Finally, the obtained crude ortho -ethoxyvinyl benzylamines are cyclized via an intramolecular reductive amination using the combination of triethylsilane/TFA to give the desired N -aryl-1,2,3,4-tetrahydroisoquinolines.
Tunable Redox Potential Photocatalyst: Aggregates of 2,3-Dicyanopyrazino Phenanthrene Derivatives for the Visible-Light-Induced α-Allylation of Amines
Bao, Ming,He, Min,Wang, Yi,Yu, Xiaoqiang
, p. 14720 - 14731 (2021/11/16)
This work highlights the tunable redox potential of 6,11-dibromo-2,3-dicyanopyrazinophenanthrene (DCPP3) aggregates, which can be formed through physical π-πstacking interactions with other DCPP3 monomers. Electrochemical and scanning electron microscopy showed that the reduction potential of [DCPP3]n aggregates could be increased by decreasing their size. The size of [DCPP3]n aggregates could be regulated by controlling the concentration of DCPP3 in an organic solvent. As such, a fundamental understanding of this tunable redox potential is essential for developing new materials for photocatalytic applications. The [DCPP3]n aggregates as a visible-light photocatalyst in combination with Pd catalysts in the visible-light-induced α-allylation of amines were used. This [DCPP3]n photocatalyst exhibits excellent photo- and electrochemical properties, including a remarkable visible-light absorption, long excited-state lifetime (16.6 μs), good triplet quantum yield (0.538), and high reduction potential (Ered([DCPP3]n/[DCPP3]n-) > -1.8 V vs SCE).
Porphyrin-Catalyzed Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones
Li, Ao,Pan, Bin,Mu, Chao,Wang, Na,Li, Yu-Long,Ouyang, Qin
supporting information, p. 679 - 684 (2021/02/01)
A visible-light-induced direct α-oxygenation of N-substituted 1,2,3,4-Tetrahydroisoquinoline derivatives has been successfully developed. Tetraphenylporphyrinatozinc(II) has been identified as an effective and inexpensive photocatalyst for this transformation with a wide range of substrates. This protocol provides a convenient route to the desired products in moderate to good yields at room temperature under air.
Solvent-driven C(sp3)-H thiocarbonylation of benzylamine derivatives under catalyst-free conditions
Zhou, Jingwei,Wang, Songping,Lu, Yaoming,Li, Lamei,Duan, Wentao,Wang, Qi,Wang, Hong,Wei, Wentao
supporting information, p. 767 - 773 (2021/02/09)
Due to the particularity of the thiocarbonyl group (C S bond), only limited C(sp3)-H thiocarbonylation methods, especially efficient and convenient methods, have been developed for the synthesis of thioamides. Inspired by the “solvent-specifici
Molecular Oxygen-Mediated Radical Alkylation of C(sp3)-H Bonds with Boronic Acids
Yang, Le,Qiu, Zhihong,Wu, Jintao,Zhao, Jianyou,Shen, Tong,Huang, Xuan,Liu, Zhong-Quan
supporting information, p. 3207 - 3210 (2021/05/04)
A direct and site-specific alkylation of (sp3)C-H bond with aliphatic boronic acid was achieved. By simply heating glycinates and amines together with alkylboronic acids under an oxygen atmosphere, a variety of unnatural α-amino acids and peptides could b
Direct Arylation of Distal and Proximal C(sp3)-H Bonds of t-Amines with Aryl Diazonium Tetrafluoroborates via Photoredox Catalysis
Mondal, Pradip Kumar,Tiwari, Sandip Kumar,Singh, Pushpendra,Pandey, Ganesh
, p. 17184 - 17196 (2021/12/02)
A visible light-mediated arylation protocol for t-amines has been reported through the coupling of γ- and α-amino alkyl radicals with different aryl diazonium salts using Ru(bpy)3Cl2·6H2O as a photocatalyst. Structurally different 9-aryl-9,10-dihydroacridine, 1-aryl tetrahydroisoquinoline, hexahydropyrrolo[2,1-a]isoquinoline, and hexahydro-2H-pyrido[2,1-a]isoquinoline frameworks with different substitution patterns have been synthesized in good yield using this methodology.
Visible-light induced Cross-Dehydrogenative-Coupling (CDC) reactions of N-aryl tetrahydroisoquinolines under aerobic conditions
Lin, Chao,Li, Peiwu,Wang, Lin
supporting information, (2021/05/19)
A visible-light induced cross-dehydrogenative-coupling (CDC) reaction of N-aryl tetrahydroisoquinolines was developed under mild aerobic conditions. This protocol proceeded smoothly with a large range of nucleophiles (nitroalkane, dimethyl phosphite, dimethyl malonate, N-methyl indole, TMSCN) under metal-free conditions and an oxygen atmosphere, forming a new C–C bond. Visible-light played a significant acceleration effect in this reaction.
