ArticleAngewandte Chemie (International ed. in English)2023
Development of a Non-Directed Petasis-Type Reaction by an Aromaticity-Disrupting Strategy.
Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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Who cites it
2 citing papers in PubMed, 7 citations in OpenAlex.
- Copper-Catalyzed Petasis-Type Reaction Enables Efficient Synthesis of C1-Substituted Tetrahydro-β-carbolines.Organic letters · 2026Article
- Strategies for the Development of Asymmetric and Non-Directed Petasis Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The Petasis-type reaction, which couples an imine and boronic acid, is an important tool for C-C bond formation in organic synthesis. However, the generality of this transformation has been limited by the requirement for a directing heteroatom to enable reactivity. Herein, we report the development of a non-directed Petasis-type reaction that allows for the coupling of trifluoroborate salts with α-hydroxyindoles. By disrupting aromaticity to generate a reactive iminium ion, in conjunction with using trifluoroborate nucleophiles, the method generates a new C-C bond without the need for a directing group. This reaction is operationally simple, providing α-functionalized indoles in up to 99 % yield using sp, sp
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