In:
Angewandte Chemie, Wiley, Vol. 135, No. 33 ( 2023-08-14)
Abstract:
Alkyne hydroamination is an effective approach for the production of enamines and enamine‐containing N ‐heterocycles. However, stereoselectivity control is a considerable challenge in this reaction because of the electronic repulsion between an incoming nitrogen lone pair and the alkyne π‐system. Herein, we propose a methodology involving β‐regio‐ and Z ‐selective alkyne hydroamination by using tetrafluoro‐λ 6 ‐sulfanyl (SF 4 ) alkynes under superbasic, naked anion conditions. The reaction is compatible with a wide variety of N ‐heterocycles, including indoles, carbazoles, pyrazoles, and imidazoles, and selectively furnishes SF 4 ‐linked Z ‐vinyl enamines with β‐regioselectively. Moreover, the method can be extended to the β‐ and Z‐ controlled, base‐mediated alkyne hydrophenoxylation with phenols to provide SF 4 ‐linked Z ‐vinyl ethers in high yields. As the SF 4 unit has attracted attention as a bioisostere for alkynes, p ‐benzenes, bicyclo[1.1.1]pentyl (BCP) groups, and cubanes in medicinal chemistry, this chemistry represents an effective approach to creating novel drug candidates incorporating SF 4 ‐containing molecules.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v135.33
DOI:
10.1002/ange.202307090
Language:
English
Publisher:
Wiley
Publication Date:
2023
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