Chromoselective access to Z- or E- allylated amines and heterocycles by a photocatalytic allylation reaction

Ana María Martínez-Gualda, Rafael Cano, Leyre Marzo, Raúl Pérez-Ruiz, Javier Luis-Barrera, Rubén Mas-Ballesté, Alberto Fraile, Víctor A. Peña O’Shea and José Alemán ()
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Ana María Martínez-Gualda: Universidad Autónoma de Madrid
Rafael Cano: Universidad Autónoma de Madrid
Leyre Marzo: Universidad Autónoma de Madrid
Raúl Pérez-Ruiz: Universitat Politècnica de València
Javier Luis-Barrera: Universidad Autónoma de Madrid
Rubén Mas-Ballesté: Universidad Autónoma de Madrid
Alberto Fraile: Universidad Autónoma de Madrid
Víctor A. Peña O’Shea: Photoactivated Processes Unit, IMDEA Energy
José Alemán: Universidad Autónoma de Madrid

Nature Communications, 2019, vol. 10, issue 1, 1-10

Abstract: Abstract The most useful strategies for the alkylation of allylic systems are related to the Tsuji–Trost reaction or the use of different Lewis acids. Herein we report a photocatalytic approach for the allylation reaction of a variety of nucleophiles, such as heteroarenes, amines and alcohols. This method is compatible with a large variety of pyrroles and indoles, containing different substituents such as electron-withdrawing and electron-donating groups, unprotected nitrogen atoms and bromo derivatives. Moreover, this methodology enables the chromoselective synthesis of Z- or E-allylated compounds. While the use of UV-light irradiation has allowed the synthesis of the previously inaccessible Z-allylated products, E-isomers are prepared simply by changing both the light source to the visible region, and the catalytic system. Based on mechanistic and photochemical proofs, laser flash photolysis studies and DFT calculations, a rational mechanism is presented.

Date: 2019
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DOI: 10.1038/s41467-019-10441-4

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