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

被引：47

作者：

Bernar, Ivan ^{[1
]}

Fiser, Bela ^{[2
,3
]}

Blanco-Ania, Daniel ^{[1
]}

Gomez-Bengo, Enrique ^{[2
]}

Rutjes, Floris P. J. T. ^{[1
]}

机构：

[1] Radboud Univ Nijmegen, Inst Mol & Mat, Heyendaalseweg 135, NL-6525 AJ Nijmegen, Netherlands

[2] Univ Basque Country UPV EHU, Dept Organ Chem 1, POB 1072, Donostia San Sebastian 20080, Spain

[3] Univ Miskolc, Inst Chem, Fac Mat Sci & Engn, H-3515 Egyetemvaros Miskolc, Hungary

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 16期

关键词：

DIVERSITY-GENERATING ELEMENT; RING-CLOSING METATHESIS; ASYMMETRIC ADDITION; PALLADIUM; ALLENES; AMINES; N; O-ACETALS; PIPERIDINES; ALKALOIDS; BONDS;

D O I：

10.1021/acs.orglett.7b01826

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：4211 / 4214

页数：4

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