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Issue 18, 2017
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Photoorganocatalytic synthesis of lactones via a selective C–H activation–alkylation of alcohols

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Abstract

Selective C–H activation is an area of growing importance in modern organic chemistry. Herein, we report our efforts in combining organocatalysis and photocatalysis for the development of a highly efficient and selective visible-light mediated protocol for the C–H activation and addition of various alcohols to a plethora of Michael acceptors, followed by a cyclization reaction leading to lactones, a repeatedly occurring motif in nature. Utilizing phenylglyoxylic acid as the photocatalyst and common household bulbs as the light source, we describe a versatile α-alkylation/lactonization of alcohols with α,β-unsaturated esters leading to products in excellent yields. The reaction mechanism was extensively studied.

Graphical abstract: Photoorganocatalytic synthesis of lactones via a selective C–H activation–alkylation of alcohols

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Publication details

The article was received on 25 Jun 2017, accepted on 16 Aug 2017 and first published on 16 Aug 2017


Article type: Paper
DOI: 10.1039/C7GC01903C
Citation: Green Chem., 2017,19, 4451-4456
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    Photoorganocatalytic synthesis of lactones via a selective C–H activation–alkylation of alcohols

    N. Kaplaneris, A. Bisticha, G. N. Papadopoulos, D. Limnios and C. G. Kokotos, Green Chem., 2017, 19, 4451
    DOI: 10.1039/C7GC01903C

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