Acid and Solvent Effects on the Regioselectivity of Minisci-Type Addition to Quinolines Using Amino-Acid-Derived Redox Active Esters
Accepted version
Peer-reviewed
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Authors
Phipps, Robert https://orcid.org/0000-0002-7383-5469
Hadrys, barbara
Abstract
Minisci-type reactions comprise an important class of reactions for the direct functionalization of basic heterocyclic compounds. On certain heterocycles, such as quinolines, Minisci-type reactions face a regioselectivity choice which often results in mixtures of regioisomers at the C2 and C4 positions, limiting utility. We present a study of the effect of solvent and Brønsted acid catalyst on regioselectivity in the addition of N-acetyl substituted, α-amino alkyl radicals to quinolines. By tuning the solvent and acid combination we identify conditions that strongly favour C2 and strongly favour C4 and present a small scope of compatible substrates.
Description
Keywords
Minisci reaction, regioselectivity, Brø, nsted acid, heterocycles, radicals
Journal Title
Synlett: accounts and rapid communications in synthetic organic chemistry
Conference Name
Journal ISSN
0936-5214
1437-2096
1437-2096
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Publisher
Thieme
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All rights reserved
Sponsorship
The Royal Society (uf130004)
European Research Council (757381)
EPSRC (2110578)
European Research Council (757381)
EPSRC (2110578)
EPSRC iCASE Studentship with GSK
Royal Society (URF)
ERC