One-Step Synthesis of Aliphatic Potassium Acyltrifluoroborates (KATs) from Organocuprates

A one-step synthesis of aliphatic KATs from organocuprates is reported. Organolithium and organomagnesium reagents were readily transmetalated onto Cu­(I) and coupled with a KAT-forming reagent to yield the respective aliphatic KAT. The protocol is suitable for primary, secondary andfor the first t...

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Published inOrganic letters Vol. 20; no. 8; pp. 2378 - 2381
Main Authors Liu, Sizhou M, Wu, Dino, Bode, Jeffrey W
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.04.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
THIOIMINIUM SALTS
ACYLBORONATE
TRIALKYLBORANES
REAGENTS
CARBONYLATION
PIPERIDINE
THIOLACTAMS
CARBON MONOXIDE
ORGANOBORANES
WATER
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Summary:A one-step synthesis of aliphatic KATs from organocuprates is reported. Organolithium and organomagnesium reagents were readily transmetalated onto Cu­(I) and coupled with a KAT-forming reagent to yield the respective aliphatic KAT. The protocol is suitable for primary, secondary andfor the first timetertiary alkyl substrates. These protocols considerably expand the range of KATs that can be readily accessed in one step from commercially available starting materials.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00720