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Aminoboranes via Tandem Iodination/Dehydroiodination for One-Pot Borylation.

ABSTRACT: A rapid synthesis of aminoboranes from amine-boranes utilizing an iodination/dehydroiodination sequence is described. Monomeric aminoboranes are generated exclusively from several substrate adducts, following an E2-type elimination, with the added base playing a critical role in monomer vs dimer formation. Diisopropylaminoborane formed using this methodology has been applied to a one-pot palladium-catalyzed conversion of iodo- and bromoarenes to the corresponding boronates. Additionally, modification of the workup allows for isolation of the boronic acid and recovery of the utilized amine.

SUBMITTER: Ramachandran PV

PROVIDER: S-EPMC9089688 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature

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Aminoboranes via Tandem Iodination/Dehydroiodination for One-Pot Borylation.

Ramachandran P Veeraraghavan PV Hamann Henry J HJ Mishra Sukriti S

ACS omega 20220414 16

A rapid synthesis of aminoboranes from amine-boranes utilizing an iodination/dehydroiodination sequence is described. Monomeric aminoboranes are generated exclusively from several substrate adducts, following an E2-type elimination, with the added base playing a critical role in monomer vs dimer formation. Diisopropylaminoborane formed using this methodology has been applied to a one-pot palladium-catalyzed conversion of iodo- and bromoarenes to the corresponding boronates. Additionally, modific ...[more]

PMID: 35573212

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