Work

Synthesis of oxaboranes via nickel-catalyzed dearylative cyclocondensation

Year: 2022

Type: article

Abstract: We report Ni-catalyzed dearylative cyclocondensation of aldehydes, alkynes, and triphenylborane. The reaction is initiated by oxidative cyclization of the aldehyde and alkyne coupling partners to generate an oxanickelacyclopentene which reacts with triphenylborane to form oxaboranes. This formal dearylative cyclocondensation reaction generates oxaboranes in moderate-to-high yields (47-99%) with high regioselectivities under mild reaction conditions. This approach represents a direct and modular synthesis of oxaboranes which are difficult to access using current methods. These oxaboranes are readily transformed into valuable building blocks for organic synthesis and an additional class of boron heterocycles. Selective homocoupling forms oxaboroles, oxidation generates aldol products, and reduction and arylation form substituted allylic alcohols.

Source: Chemical Science

DOI: 10.1039/d2sc01840c

Authors: Mason T. Koeritz, Haley K. Banovetz, Sean A. Prell, Levi M. Stanley

Institution: Iowa State University

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: National Science Foundation, Iowa State University, Division of Chemistry

Awards: G3460184781, Catalytic Alkene Carbofunctionalization and Carbodifunctionalization: Catalyst Identification, Reaction Development, and Mechanistic Insights