Weak Base-Promoted Direct Cross-Coupling of Naphthalene-1,8-diaminato-substituted Arylboron Compounds.

ABSTRACT: The indispensability of a base in Suzuki-Miyaura coupling (SMC) employing organoboronic acids/esters is well recognized, which occasionally induces competitive protodeborylation in organoboron reagents. This phenomenon is particularly pronounced in fluorine-substituted aryl and heteroaryl boron compounds. Here, we show that direct SMC of naphthalene-1,8-diaminato (dan)-substituted aryl boron compounds, Ar-B(dan), characterized by its remarkable stability toward protodeborylation due to their diminished boron-Lewis acidity, occurs utilizing a weak base in conjunction with a palladium/copper cooperative catalyst system. The approach delineated in this study enables the efficient incorporation of various perfluoroaryl- and heteroaryl-B(dan) reagents, while maintaining high functional group to

SUBMITTER: Tomota K 

PROVIDER: S-EPMC11522924 | biostudies-literature | 2024 Oct

REPOSITORIES: biostudies-literature