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

Autor:	Giorgos N. Papadopoulos, Aikaterini Bisticha, Dimitris Limnios, Christoforos G. Kokotos, Nikolaos Kaplaneris
Rok vydání:	2017
Předmět:	Reaction mechanism Phenylglyoxylic acid 010405 organic chemistry Chemistry Alkylation 010402 general chemistry 01 natural sciences Pollution 0104 chemical sciences chemistry.chemical_compound Light source Organocatalysis Photocatalysis Environmental Chemistry Organic chemistry
Zdroj:	Green Chemistry. 19:4451-4456
ISSN:	1463-9270 1463-9262
DOI:	10.1039/c7gc01903c
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::bdf436d22d9e413abd10ea10a809932a https://doi.org/10.1039/c7gc01903c Zobrazit plný text záznamu