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

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

A novel photoinduced Fe­(OTf)2/2,4,6-collidine-catalyzed alkylation of Morita–Baylis–Hillman (MBH) acetates using carboxylic acids in a regio- and stereoselective manner is reported. This method demonstrates a broad scope, encompassing various carboxylic acids and MBH acetates, including drugs and b...

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Veröffentlicht in:Organic letters 2024-10, Vol.26 (40), p.8583-8588
Hauptverfasser: Golagani, Durga, Prakash, Kota Krishna, Thapa, Satyam, Sai Naik, Mudavath Bhargav, Akondi, Srirama Murthy
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container_end_page 8588
container_issue 40
container_start_page 8583
container_title Organic letters
container_volume 26
creator Golagani, Durga
Prakash, Kota Krishna
Thapa, Satyam
Sai Naik, Mudavath Bhargav
Akondi, Srirama Murthy
description A novel photoinduced Fe­(OTf)2/2,4,6-collidine-catalyzed alkylation of Morita–Baylis–Hillman (MBH) acetates using carboxylic acids in a regio- and stereoselective manner is reported. This method demonstrates a broad scope, encompassing various carboxylic acids and MBH acetates, including drugs and bioactive molecules, to synthesize densely functionalized cinnamates and acrylates. The reactions are performed in the green solvent dimethyl carbonate under oxidant-free conditions. Based on control experiments, a plausible mechanism involving an Fe­(II)–Fe­(III)–Fe­(II) cycle is proposed.
doi_str_mv 10.1021/acs.orglett.4c03216
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title Visible-Light-Promoted Iron(II)/Lewis Base Catalysis for the Alkylation of Morita–Baylis–Hillman Acetates Using Carboxylic Acids
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