Pd-Catalyzed regioselective iminothiolation of alkynes: A remarkable effect of the CF3 group of iminosulfides

Organic Letters

Volumn 12, Issue 17, 2010, Pages 3744-3747

  Minami, Yasunori ^a   Kuniyasu, Hitoshi ^a   Sanagawa, Atsushi ^a   Kambe, Nobuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77956198681     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101289k     Document Type: Article

References (31)

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20. The high reactivity and regioselectivity would be attributed to the oxygen atom at the propargyl moiety in alkynes; see ref 5a.
21. When the reaction of 1a and 2a was performed at 100 °C in a sealed vessel without a microwave irradiation, 3a was obtained in a E to Z ratio of 93:7 with the same yield, indicating that following isomerization of the adducts was partly prevented by the microwave irradiation.
22. 3, R = 0.0661, and Rw = 0.189. See Supporting Informaion for crystal data for E-3a.
23. 8 solution at -40 °C appeared as a mixture of two stereoisomers by slow inversion of the N lone pair on the imino group in a ratio of 75:25 (stereochemistry undetermined).
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31. Monitoring the reaction of 1a with 2h at room temperature showed that the cis: trans ratio of 3o stayed the same during the course of the reaction, implicating that trans-3 was produced through isomerisation of cis-8 to trans-8 prior to the reductive elimination.