Work

Photoredox Catalysis Enables Access to N-Functionalized 2,1-Borazaronaphthalenes

Year: 2019

Type: article

Abstract: The synthesis and utilization of a class of 2,1-borazaronaphthyltrifluoroborate reagents that provide a general solution to the challenge of N-functionalization of the 2,1-borazaronaphthalene core is described. By adorning the nitrogen of this core with a trifluoroboratomethyl unit, a suite of odd-electron processes can be executed, installing motifs that would otherwise be inaccessible using a two-electron approach. In addition, this process enables rapid annulation, furnishing a heretofore unknown polycyclic B-N species.

Source: Organic Letters

DOI: 10.1021/acs.orglett.9b00884

Authors: Xie Wang, Geraint H. M. Davies, Adriel Koschitzky, Steven R. Wisniewski, Christopher B. Kelly, Gary A. Molander

Institutions: Hunan University, State Key Laboratory of Chemobiosensing and Chemometrics, University of Pennsylvania, Virginia Commonwealth University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Virginia Commonwealth University, China Scholarship Council, National Institute of General Medical Sciences

Awards: Novel Borazines: Syntheses and Elaboration, A Novel Mechanistic Paradigm for Cross-Coupling, Accessing New Chemical Space via Organic Synthesis, Non-Organometallic Partners as Radical Precursors for the Diversification of Dual Catalytic Cross-Coupling Processes