Bidentate Phosphine Ligand Impacts on Previously Inaccessible 5-Membered N-Heteroaryne Formation and Functionalization.

ABSTRACT: 5-Membered N-heteroarynes have long been considered synthetically inaccessible; however, we recently reported the use of a bisphosphine-ligated nickel center to stabilize and enable the formation of these otherwise unobtainable intermediates. Motivated by this success, we were compelled to study the role of the ancillary phosphine in aryne formation and reactivity. Herein, a set of four bidentate phosphine ligands with altered phosphine substituents and backbone length are interrogated for their competence as ancillary ligands for 5-membered N-heteroaryne formation. We determined that ligands with phenyl phosphine substituents or linker lengths longer than three carbons were unsuitable for this purpose, while ligands having alkyl phosphine substituents and one, two, or three carbon linkers

SUBMITTER: Plasek EE 

PROVIDER: S-EPMC12410832 | biostudies-literature | 2024 Oct

REPOSITORIES: biostudies-literature