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Indium–Organic Framework with <i>soc</i> Topology as a Versatile Catalyst for Highly Efficient One-Pot Strecker Synthesis of α-aminonitriles

Gaurav Verma, Katherine A. Forrest, Benjamin A. Carr, Harsh Vardhan, Junyu Ren, Tony Pham, Brian Space, Sanjay Kumar, Shengqian Ma

2021ACS Applied Materials & Interfaces41 citationsDOI

Abstract

An In(III) based metal–organic framework (MOF), In-pbpta, with soc topology was constructed from the trigonal prismatic [In3(μ3-O)(H2O)3(O2C−)6] secondary building unit (SBU) and a custom-designed tetratopic linker H4pbpta (pbpta = 4,4′,4″,4‴-(1,4-phenylenbis(pyridine-4,2,6-triyl))-tetrabenzoic acid)). The obtained MOF shows a Brunauer–Emmett–Teller surface area of 1341 m2/g with a pore volume of 0.64 cm3/g, which is the highest among the scarcely reported In-soc-MOFs. The constructed MOF demonstrates excellent performance as a heterogeneous Lewis acid catalyst for highly efficient conversion in a one-pot multicomponent Strecker reaction for the preparation of α-aminonitriles under solvent-free conditions, which can be easy to separate and recycle without significant loss of activity for up to seven cycles. The computational modeling studies suggest the presence of the three substrates in close vicinity to the In-oxo cluster. The strong interactions of the aldehyde/ketone and the amine with the In-oxo cluster together with the readily available cyanide ion around the In-oxo cluster lead to high catalytic conversion within a short period of time for the MOF catalyst. Our work therefore lays a foundation to develop MOF as a new class of efficient heterogeneous catalyst for one-pot Strecker reaction.

Topics & Concepts

Strecker amino acid synthesisCatalysisMaterials scienceAldehydeMetal-organic frameworkMesoporous materialIndiumKetoneTopology (electrical circuits)Lewis acids and basesHeterogeneous catalysisOrganic chemistryChemistryEnantioselective synthesisAdsorptionMathematicsMetallurgyCombinatoricsMetal-Organic Frameworks: Synthesis and ApplicationsChemical Synthesis and ReactionsOrganometallic Compounds Synthesis and Characterization