Synthesis of Fluorinated Aminoalkylboronic Acids from Amphoteric α‐Boryl Aldehydes

Autor:	Andrei K. Yudin, Harjeet S. Soor, Katherine I. Burton, Diego B. Diaz
Rok vydání:	2021
Předmět:	010405 organic chemistry Hydrogen bond Electrophilic fluorination General Medicine General Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Functional group Ph range Degradation (geology) Molecule
Zdroj:	Angewandte Chemie International Edition. 60:16366-16371
ISSN:	1521-3773 1433-7851
DOI:	10.1002/anie.202104133
Popis:	Our ongoing search for underdeveloped functional group combinations has brought to light α-fluorinated aminoalkylboronic acids, a new class of molecules featuring the B-CF linkage. These compounds can now be generated from secondary amines and α-boryl aldehydes through electrophilic fluorination of boryl enamines or enamides. Fluorinated β-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 β-aminoalkylboronic acids are stable over a wide pH range and are characterized by a pKa of 3.4, which is the lowest of any alkylboronic acid.
Databáze:	OpenAIRE
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