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- Title
One‐Pot Successive Turbo Grignard Reactions for the Facile Synthesis of α‐Aryl‐α‐Trifluoromethyl Alcohols.
- Authors
Kani, Ryunosuke; Inuzuka, Toshiyasu; Kubota, Yasuhiro; Funabiki, Kazumasa
- Abstract
A novel straightforward one‐pot methodology for two successive turbo Grignard reagent (iPrMgCl·LiCl) reactions, was developed for a facile synthesis of α‐aryl‐α‐trifluoromethyl alcohols, motifs of value in pharmaceutical chemistry. The method displayed broad functional group tolerance, including reducible groups. Dual roles of iPrMgCl·LiCl were exploited in the tandem reaction with commercially available iodoarenes or iodoheteroarenes and 2,2,2‐trifluoroethyl trifluoroacetate. The process encompasses three successive reactions in a one‐pot process: the iPrMgCl·LiCl‐mediated iodine/magnesium‐exchange reaction of iodoarenes or iodoheteroarenes; nucleophilic addition of various generated aryl or heteroarylmagnesium reagents to 2,2,2‐trifluoroethyl trifluoroacetate; and the reduction of in‐situ generated aryl trifluoromethyl ketones with iPrMgCl·LiCl, to produce the corresponding α‐aryl or α‐heteroaryl‐α‐trifluoromethyl alcohols bearing various substituents, including reducible functional groups in good to excellent yields.
- Subjects
GRIGNARD reagents; PHARMACEUTICAL chemistry; FUNCTIONAL groups; ALCOHOL; TRIFLUOROACETIC acid; HYPERVALENCE (Theoretical chemistry)
- Publication
European Journal of Organic Chemistry, 2020, Vol 2020, Issue 29, p4487
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202000550