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N-Heterocyclic Iod(az)olium Salts - Potent Halogen-Bond Donors in Organocatalysis.

ABSTRACT: This article describes the application of N-heterocyclic iod(az)olium salts (NHISs) as highly reactive organocatalysts. A variety of mono- and dicationic NHISs are described and utilized as potent XB-donors in halogen-bond catalysis. They were benchmarked in seven diverse test reactions in which the activation of carbon- and metal-chloride bonds as well as carbonyl and nitro groups was achieved. N-methylated dicationic NHISs rendered the highest reactivity in all investigated catalytic applications with reactivities even higher than all previously described monodentate XB-donors based on iodine(I) and (III) and the strong Lewis acid BF₃ .

SUBMITTER: Boelke A

PROVIDER: S-EPMC8519039 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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N-Heterocyclic Iod(az)olium Salts - Potent Halogen-Bond Donors in Organocatalysis.

Boelke Andreas A Kuczmera Thomas J TJ Lork Enno E Nachtsheim Boris J BJ

Chemistry (Weinheim an der Bergstrasse, Germany) 20210805 52

This article describes the application of N-heterocyclic iod(az)olium salts (NHISs) as highly reactive organocatalysts. A variety of mono- and dicationic NHISs are described and utilized as potent XB-donors in halogen-bond catalysis. They were benchmarked in seven diverse test reactions in which the activation of carbon- and metal-chloride bonds as well as carbonyl and nitro groups was achieved. N-methylated dicationic NHISs rendered the highest reactivity in all investigated catalytic applicati ...[more]

PMID: 34160859

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