Palladium-catalyzed oxidative C-H activation/annulation of -alkylanilines with bromoalkynes: access to functionalized 3-bromoindoles.

Chem Commun (Camb)

State Key Laboratory of Luminescent Materials and Devices, Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China.

Published: August 2022

A straightforward approach to the synthesis of 3-bromoindoles palladium-catalyzed oxidative C-H activation/annulation of -alkylanilines with bromoalkynes has been described. This protocol features high atom economy, excellent chemo- and regioselectivities, and good functional group tolerance. Moreover, the resultant 3-bromoindoles can be transformed to various functionalized indole derivatives, which demonstrates the practicability of this method in organic synthesis.

Download full-text PDF

Source
http://dx.doi.org/10.1039/d2cc03298hDOI Listing

Publication Analysis

Top Keywords

palladium-catalyzed oxidative
8
oxidative c-h
8
c-h activation/annulation
8
activation/annulation -alkylanilines
8
-alkylanilines bromoalkynes
8
bromoalkynes access
4
access functionalized
4
functionalized 3-bromoindoles
4
3-bromoindoles straightforward
4
straightforward approach
4

Similar Publications

Palladium-Catalyzed Oxidative Allene-Allene Cross-Coupling.

J Am Chem Soc

January 2025

Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-10691 Stockholm, Sweden.

Direct cross-coupling reactions between two similar unactivated partners are challenging but constitute a powerful strategy for the creation of new carbon-carbon bonds in organic synthesis. [4]Dendralenes are a class of acyclic branched conjugated oligoenes with great synthetic potential for the rapid generation of structural complexity, yet the chemistry of [4]dendralenes remains an unexplored field due to their limited accessibility. Herein, we report a highly selective palladium-catalyzed oxidative cross-coupling of two allenes with the presence of a directing olefin in one of the allenes, enabling the facile synthesis of a broad range of functionalized [4]dendralenes in a convergent modular manner.

View Article and Find Full Text PDF

An aryl radical assay is used to provide information about the formation of aryl radicals from aryl halides in coupling reactions to arenes in the presence of palladium sources and under LED irradiation (λ = 456 nm). The assay uses 2-halo--xylenes as substrates. Aryl radical formation is indicated both by a defined product composition and by signature deuterium isotope effects.

View Article and Find Full Text PDF

Under most conditions, 2,4-dihalopyrimidines undergo substitution reactions at C4. Here we report that Pd(II) precatalysts supported by bulky -heterocyclic carbene ligands uniquely effect C2-selective cross-coupling of 2,4-dichloropyrimidine with thiols. The regioselectivity of this reaction stands in stark contrast to ∼1500 previously reported Pd-catalyzed cross-couplings that favor C4 in the absence of other substituents on the pyrimidine ring.

View Article and Find Full Text PDF

Theoretical Studies on the Reaction Mechanism for the Cycloaddition of Zwitterionic π-Allenyl Palladium Species: Substrate-Controlled Isomerization.

Molecules

December 2024

State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Zwitterionic π-allenyl palladium species are newly developed intermediates. A substrate-controlled step existed in the cycloaddition of zwitterionic π-allenyl palladium species with tropsulfimides or tropones. With the assistance of previously experimental studies, zwitterionic allenyl/propargyl palladium species was provenly found by HRMS.

View Article and Find Full Text PDF

A synthetic strategy of a palladium-catalyzed cascade annulation reaction followed by aerial oxidation was designed to construct 6-benzo[c]chromene scaffolds. Various 6-benzo[c]chromenes were synthesized under mild reaction conditions using easily accessible -QMs and commercially available -hydroxyarylboronic acids. One of the synthesized chromenes has been ambiguously confirmed by single-crystal XRD analysis.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!