期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 30, 页码 16366-16371出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202104133
关键词
aminoalkylboronic acids; electrophilic fluorination; fluorine-containing boronic acids; alpha-boryl aldehydes
资金
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- NSERC
The ongoing search for underdeveloped functional group combinations has led to the discovery of alpha-fluorinated aminoalkylboronic acids, a new class of molecules featuring the B-CF linkage. These compounds can be generated through electrophilic fluorination and show stability and unique structural properties.
Our ongoing search for underdeveloped functional group combinations has brought to light alpha-fluorinated aminoalkylboronic acids, a new class of molecules featuring the B-CF linkage. These compounds can now be generated from secondary amines and alpha-boryl aldehydes through electrophilic fluorination of boryl enamines or enamides. Fluorinated beta-aminoalkylboronic acids show no signs of degradation under ambient conditions. We present evidence for the involvement of chair-like motifs, favored over the acyclic forms by up to 1.7 +/- 0.1 kcal mol(-1) in water and held together by an amine-boronate hydrogen bond. Fluorinated beta-aminoalkylboronic acids are stable over a wide pH range and are characterized by a pK(a) of 3.4, which is the lowest of any alkylboronic acid.
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