ArticleJournal of the American Chemical Society2020
Chemo- and Regioselective Synthesis of Acyl-Cyclohexenes by a Tandem Acceptorless Dehydrogenation-[1,5]-Hydride Shift Cascade.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 43 citations in OpenAlex.
- Formal Hydride Abstraction: A Unified Photoredox Platform for Nucleophilic C(sp3)-H Functionalization.Accounts of chemical research · 2026Article
- Asymmetric Hydride Shift Reactions Catalyzed by Chiral Aluminium Complexes.Angewandte Chemie (International ed. in English) · 2026Article
- Redox Reorganization: Aluminium Promoted 1,5-Hydride Shifts Allow the Controlled Synthesis of Multisubstituted Cyclohexenes.Angewandte Chemie (International ed. in English) · 2023Article
- Synthesis of Cyclopropanes via Hydrogen-Borrowing Catalysis.Organic letters · 2023Article
- Evolution of the Dearomative Functionalization of Activated Quinolines and Isoquinolines: Expansion of the Electrophile Scope.Angewandte Chemie (International ed. in English) · 2022Article
- Evolution of the Dearomative Functionalization of Activated Quinolines and Isoquinolines: Expansion of the Electrophile Scope.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Article
- Crossed Regio- and Enantioselective Iron-Catalyzed [4+2]-Cycloadditions of Unactivated Dienes.Angewandte Chemie (International ed. in English) · 2022Article
- Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids.Angewandte Chemie (International ed. in English) · 2021Article
- Control of Absolute Stereochemistry in Transition-Metal-Catalysed Hydrogen-Borrowing Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Review
- A Vinyl Cyclopropane Ring Expansion and Iridium-Catalyzed Hydrogen Borrowing Cascade.Angewandte Chemie (International ed. in English) · 2020Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
An atom-economical methodology to access substituted acyl-cyclohexenes from pentamethylacetophenone and 1,5-diols is described. This process is catalyzed by an iridium(I) catalyst in conjunction with a bulky electron rich phosphine ligand (CataCXium A) which favors acceptorless dehydrogenation over conjugate reduction to the corresponding cyclohexane. The reaction produces water and hydrogen gas as the sole byproducts and a wide range of functionalized acyl-cyclohexene products can be synthesized using this method in very high yields. A series of control experiments were carried out, which revealed that the process is initiated by acceptorless dehydrogenation of the diol followed by a redox-neutral cascade process, which is independent of the iridium catalyst. Deuterium labeling studies established that the key step of this cascade involves a novel base-mediated [1,5]-hydride shift. The cyclohexenyl ketone products could readily be cleaved under mildly acidic conditions to access a range of valuable substituted cyclohexene derivatives.
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Registered trials
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