A new [Au(I)] catalyzed intramolecular hydrocarboxylation of allenes is presented as a valuable synthetic route to oxazino-indolones. The use of 3,5-(CF3)2–C6H3–ImPyAuSbF6 as the optimal catalyst (5 mol%) was necessary to guarantee (i) wide tolerance of functional groups, (ii) mild reaction conditions (r.t., 16 h), and (iii) high yields (up to 90%). Preliminary attempts towards an enantioselective version (81 : 19 er) are also documented by means of a new family of chiral C1-symmetric ImPyAuCl complexes.

Convenient synthesis of polycyclic N(1)-C(2)-fused oxazino-indolones via [Au(I)] catalyzed hydrocarboxylation of allenes / Riccardo Pedrazzani, Emanuele Pinosa, Giulio Bertuzzi, Magda Monari, Samuel Lauzon, Thierry Ollevier, Marco Bandini. - In: CHEMICAL COMMUNICATIONS. - ISSN 1364-548X. - ELETTRONICO. - 58:(2022), pp. 8698-8701. [10.1039/D2CC02303B]

Convenient synthesis of polycyclic N(1)-C(2)-fused oxazino-indolones via [Au(I)] catalyzed hydrocarboxylation of allenes

Riccardo Pedrazzani;Emanuele Pinosa;Giulio Bertuzzi;Magda Monari;Thierry Ollevier;Marco Bandini
2022

Abstract

A new [Au(I)] catalyzed intramolecular hydrocarboxylation of allenes is presented as a valuable synthetic route to oxazino-indolones. The use of 3,5-(CF3)2–C6H3–ImPyAuSbF6 as the optimal catalyst (5 mol%) was necessary to guarantee (i) wide tolerance of functional groups, (ii) mild reaction conditions (r.t., 16 h), and (iii) high yields (up to 90%). Preliminary attempts towards an enantioselective version (81 : 19 er) are also documented by means of a new family of chiral C1-symmetric ImPyAuCl complexes.
2022
Convenient synthesis of polycyclic N(1)-C(2)-fused oxazino-indolones via [Au(I)] catalyzed hydrocarboxylation of allenes / Riccardo Pedrazzani, Emanuele Pinosa, Giulio Bertuzzi, Magda Monari, Samuel Lauzon, Thierry Ollevier, Marco Bandini. - In: CHEMICAL COMMUNICATIONS. - ISSN 1364-548X. - ELETTRONICO. - 58:(2022), pp. 8698-8701. [10.1039/D2CC02303B]
Riccardo Pedrazzani, Emanuele Pinosa, Giulio Bertuzzi, Magda Monari, Samuel Lauzon, Thierry Ollevier, Marco Bandini
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/900627
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