Visible-Light-Promoted Iron(II)/Lewis Base Catalysis\nfor the Alkylation of Morita–Baylis–Hillman Acetates\nUsing Carboxylic Acids

A novel photoinduced Fe(OTf)<sub>2</sub>/2,4,6-collidine-catalyzed\nalkylation of Morita–Baylis–Hillman (MBH) acetates using\ncarboxylic acids in a regio- and stereoselective manner is reported.\nThis method demonstrates a broad scope, encompassing various carboxylic\nacids and MBH acetates, including drugs and bioactive molecules, to\nsynthesize densely functionalized cinnamates and acrylates. The reactions\nare performed in the green solvent dimethyl carbonate under oxidant-free\nconditions. Based on control experiments, a plausible mechanism involving\nan Fe(II)–Fe(III)–Fe(II) cycle is proposed.

Publication Details

Journal
Figshare
Published
2024-10-01
DOI
https://doi.org/10.1021/acs.orglett.4c03216.s001
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Visible-Light-Promoted Iron(II)/Lewis Base Catalysis\nfor the Alkylation of Morita–Baylis–Hillman Acetates\nUsing Carboxylic Acids

Figshare
Radical Photochemical Reactions
article

Visible-Light-Promoted Iron(II)/Lewis Base Catalysis\nfor the Alkylation of Morita–Baylis–Hillman Acetates\nUsing Carboxylic Acids

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Abstract

A novel photoinduced Fe(OTf)<sub>2</sub>/2,4,6-collidine-catalyzed\nalkylation of Morita–Baylis–Hillman (MBH) acetates using\ncarboxylic acids in a regio- and stereoselective manner is reported.\nThis method demonstrates a broad scope, encompassing various carboxylic\nacids and MBH acetates, including drugs and bioactive molecules, to\nsynthesize densely functionalized cinnamates and acrylates. The reactions\nare performed in the green solvent dimethyl carbonate under oxidant-free\nconditions. Based on control experiments, a plausible mechanism involving\nan Fe(II)–Fe(III)–Fe(II) cycle is proposed.

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Radical Photochemical Reactions
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Visible-Light-Promoted Iron(II)/Lewis Base Catalysis\nfor the Alkylation of Morita–Baylis–Hillman Acetates\nUsing Carboxylic Acids · Figshare (2024) | TGRS Research Map | TGRS