Copper‐Catalyzed Oxygenative Skeletal Rearrangement of Tetrahydro‐β‐carbolines Using H2O and O2 as Oxygen Sources DOI Open Access

Yusheng Peng,

Wei Wang, Jun Shi

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(51)

Published: Nov. 11, 2023

Abstract Herein, we report an unprecedented skeletal rearrangement reaction of tetrahydro‐ β ‐carbolines enabled by copper‐catalyzed single‐electron oxidative oxygenation, in which H 2 O and act as oxygen sources to generate a unique 2‐hydroxyl‐3‐peroxide indoline intermediate. The synthetic reactivity species was demonstrated multi‐step bond cleavage formation cascade. Using readily available copper catalyst under open‐air conditions, highly important yet synthetically difficult spiro[pyrrolidone‐(3,1‐benzoxazine)] products were obtained single operation. utility this methodology is the efficient synthesis natural donaxanine chimonamidine, well 3‐hydroxyl‐pyrroloindoline scaffold, just one or two steps.

Language: Английский

Silver-Enabled Dearomative Trifluoromethoxylation of Indoles DOI
Zhijie Deng,

Lingduan Meng,

Bing Xiao

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(4), P. 2325 - 2332

Published: Jan. 17, 2024

The only known method for the dearomative trifluoromethoxylation of indoles is preliminary, with one substrate successfully undergoing reaction. In this study, we not developed a broadly applicable indole but also achieved divergent by fine-tuning reaction conditions. Under optimized conditions, silver salt and an easily handled OCF3 reagent, various smoothly underwent dearomatization to afford diverse array ditrifluoromethoxylated indolines in 50–84% isolated yields up 37:1 diastereoselectivity, fluorinated trifluoromethoxylated were obtained exclusive trans selectivity. addition, conditions compatible other heteroaromatic rings as well styrene moieties.

Language: Английский

Citations

11

Manganese-Catalyzed Electrochemical Oxidation of Tryptophan-Containing Peptides and Indole Derivatives by O2 DOI
Min Xu, Qin He, Xiaojiang Li

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 3928 - 3939

Published: Feb. 20, 2025

Language: Английский

Citations

2

Benzylic C(sp3)–H Functionalization via Copper-Catalyzed [3+3] Radical Cycloaddition DOI
Jun Shi,

Xiong-Jiang Li,

Shu-Yun Jiang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(8), P. 5605 - 5611

Published: March 29, 2024

The development of benzylic C(sp3)–H functionalization methods for the assembly derivatives has been extensively explored in recent years. However, engagement carbon and its adjacent C=C bond as a C3 synthon cycloaddition reaction via direct C–H activation is rare. Herein, we report copper-catalyzed [3+3] radical through to construct six-membered cyclohexane-type rings. In this reaction, 2-benzylic an indole selectively activated serves that reacts highly chemoselective intermolecular self-[3+3] cross-[3+3] pathways. Multiple symmetric nonsymmetric polycyclic hexahydrocarbazole scaffolds with hexacyclic 6/5/5/6/5/5/6 pentacyclic 6/5/5/6/5/6 ring systems are synthesized high efficiency chemoselectivity using strategy. Inspired by unique addition pathway cycloaddition, controllable construction C3a-alkylated pyrroloindolines was also developed.

Language: Английский

Citations

6

1,2-Redox Transpositions of Tertiary Amides DOI Creative Commons
Benjamin D. A. Shennan,

Sergio Sánchez-Alonso,

Gabriele Rossini

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(40), P. 21745 - 21751

Published: Sept. 27, 2023

Reactions capable of transposing the oxidation levels adjacent carbon atoms enable rapid and fundamental alteration a molecule's reactivity. Herein, we report 1,2-transposition atom level in cyclic acyclic tertiary amides, resulting one-pot synthesis 1,2- 1,3-oxygenated amines. This transfer was facilitated by careful orchestration an iridium-catalyzed reduction with functionalization transiently formed enamine intermediates. A novel 1,2-carbonyl transposition is described, breadth this redox strategy has been further explored development aminoalcohol enaminone syntheses. The diverse β-functionalized amine products were shown to be multifaceted valuable synthetic intermediates, accessing challenging biologically relevant motifs.

Language: Английский

Citations

12

Copper/Iodine Co-catalyzed Oxygenative Transannulation of Tryptamines Enables Direct Synthesis of Donaxaridine and Its Derivatives DOI

Yan-Zheng Sun,

Ying-Ai Wu,

Jun Shi

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(3), P. 625 - 630

Published: Jan. 11, 2024

We report a general copper/iodine co-catalyzed oxygenative transannulation strategy using readily available tryptamines. Molecular oxygen and water are used as sources provide direct access to the donaxaridine scaffold its derivatives. This methodology is applied efficient synthesis of natural products donaxaridine, chimonamidine, donaxanine, donaxarine, aline in just one or two steps. The tryptamines, albeit with oxy-sensitive dialkyl N-H groups, selectively oxidized through single-electron transfer dioxygenation process.

Language: Английский

Citations

5

An electrolyte additive of bromoxoindole enables uniform Li-ion flux and tunable Li2S deposition for high-performance lithium–sulfur batteries DOI

Jinxuan Zou,

Pengxuan He,

Yufang Zhang

et al.

Journal of Materials Chemistry A, Journal Year: 2024, Volume and Issue: 12(9), P. 5520 - 5529

Published: Jan. 1, 2024

6-Bromoxoindole, an electrolyte additive, enables the lithium–sulfur battery to operate stably under high-loading, lean-electrolyte, and low-temperature conditions simultaneously.

Language: Английский

Citations

4

Rh(III)-Catalyzed Indole Dearomative 1,2-Alkoxyl Shift Rearrangement DOI
Can Yang,

Lixing Shen,

Ying Xie

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 9, 2025

A Rh(III)-catalyzed dearomative C3 alkoxylation of indoles via cascade C(sp2)-H activation and 1,2-alkoxyl shift rearrangement has been developed. This method provides an efficient strategy to rapidly assemble 3-alkoxyindolin-2-one scaffolds using alcohols as alkoxyl sources. Mechanistic studies indicate that indolyl C2 followed by Ag(I)/Cu(II)-mediated migration is involved in this transformation.

Language: Английский

Citations

0

Assembly of 3-Halooxindoles via Interrupted Semipinacol Rearrangement: Enabling Concise Total Synthesis of CPC-1 DOI
Yaoyao Liu, Yating Zhang,

Fan Zhang

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134672 - 134672

Published: April 1, 2025

Language: Английский

Citations

0

Single-electron transfer enables enantioselective synthesis of spirooxindoles via dual copper and phosphoric acid catalysis DOI
Jun Shi, Xueting Zhou, Bingqing Yang

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111250 - 111250

Published: April 1, 2025

Language: Английский

Citations

0

Construction of 3-Hydroxyindolin-2-ones via Ru(II)-Catalyzed Domino Alkylation/Cyclization/Oxidation of 2-Aminophenethanols DOI

Chuanhu Wang,

Huang Jing-wen,

Bo Deng

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 24, 2025

A novel Ru(II)-catalyzed domino reaction, comprising alkylation, cyclization, and oxidation of 2-aminophenethanols with benzyl alcohols, has been developed for the synthesis 3-hydroxyindolin-2-ones. This transformation exhibits excellent synthetic efficiency, enabling selective formation four or three σ bonds, one π bond, quaternary carbon center in step under identical conditions. Furthermore, it provides a versatile approach to 3-hydroxyindolin-2-one frameworks distinct substituents at 1- 3-positions.

Language: Английский

Citations

0