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

Ivan Bernar | Zendy; Béla Fiser | Zendy; Daniel BlancoAnia | Zendy; Enrique GómezBengoa | Zendy; Floris P. J. T. Rutjes | Zendy

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

Author(s) -

Ivan Bernar,

Béla Fiser,

Daniel BlancoAnia,

Enrique GómezBengoa,

Floris P. J. T. Rutjes

Publication year - 2017

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b01826

Subject(s) - chemistry , hydroamination , azole , allene , protonation , catalysis , palladium , nucleophile , combinatorial chemistry , enantioselective synthesis , sulfonamide , stereochemistry , medicinal chemistry , organic chemistry , antifungal , medicine , ion , dermatology

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 2 ), which develops a strongly nucleophilic character at the central C atom.

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