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

ABSTRACT: 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.

SUBMITTER: Bernar I

PROVIDER: S-EPMC5565904 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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

Bernar Ivan I Fiser Béla B Blanco-Ania Daniel D Gómez-Bengoa Enrique E Rutjes Floris P J T FPJT

Organic letters 20170808 16

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-PdL<sub>2</sub>), which develops a strongly nucleophilic character at the central C atom. ...[more]

PMID: 28786679

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