Organic Letters
Organic Letters
5 years ago

Pd-Catalyzed Hydroamination of Alkoxyallenes with Azole Heterocycles: Examples and Mechanistic Proposal

Pd-Catalyzed Hydroamination of Alkoxyallenes with Azole Heterocycles: Examples and Mechanistic Proposal
Floris P. J. T. Rutjes, Enrique Gómez-Bengoa, Ivan Bernar, Béla Fiser, Daniel Blanco-Ania
Palladium-catalyzed regio- and enantioselective addition of azole heterocycles to alkoxyallenes was developed (up to 92% yields and up to 94% ee). DFT calculations suggest a new Pd(0)-driven mechanistic pathway proceeding through protonation of the Pd-coordinated allene (4-PdL2), which develops a strongly nucleophilic character at the central C atom.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01826

DOI: 10.1021/acs.orglett.7b01826

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