Abstract
This work proposes a new method for the synthesis of N-borylated amino acids based on nucleophilic substitution reactions in the [B12H11IPh]– anion. Esters of glycine and L-phenylalanine were used as nucleophiles. The structure of the products has been determined by multinuclear NMR spectroscopy, IR spectroscopy, and ESI mass spectrometry.
Highlights
Boron cluster anions are widely used as components of photovoltaic devices [1,2,3,4,5,6], catalysts [7, 8], biosensors [9, 10], and molecular magnets [11, 12]
Halonium ions are one of the types of such groups, which can react with a number of nucleophilic reagents. This approach was successfully extended to iodonium derivatives of carboranes [27], which react with various nucleophiles with selective substitution of the arylgalonium substituent
Iodonium derivatives can enter into substitution reactions of PhI groups with a number of nucleophiles [31,32,33,34,35]
Summary
Boron cluster anions are widely used as components of photovoltaic devices [1,2,3,4,5,6], catalysts [7, 8], biosensors [9, 10], and molecular magnets [11, 12]. The use of iodonium functional substituents as leaving (ipso) groups is a rather powerful tool for creating new boron-containing compounds with a given set of properties. In this regard, the aim of this work was the creation of new substituted derivatives of the closo-dodecaborate anion and natural amino acids based on the processes of nucleophilic substitution in the [B12H11IPh]– anion. PhI(OAc) (0.77 g, 2.4 mmol) was added to the resulting solution, and the reaction mixture was stirred in an atmosphere of dry argon with moderate heating (up to 40°C) for 2 h.
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