学術雑誌論文

学術雑誌論文

text

ACS Catalysis. 2025, 15(21), p. 18077-18086

Enantioselective Heterocoupling of 2-Naphthylamines with 2-Naphthol Derivatives via Cooperative Photoactivation and Chiral Vanadium(V) Catalysis

American Chemical Society

英語

text

2025-10-17

https://doi.org/10.1021/acscatal.5c05038

This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acscatal.5c05038

The photoactivated heterocoupling of 2-naphthylamines with 2-naphthols/3-phenanthrols under LED light irradiation in the presence of a mononuclear chiral vanadium complex was established. The protocol features high cross-coupling selectivity and atom economy, affording various 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN) derivatives in up to 95% yields with 90:10 enantiomeric ratio using equimolar ratios of coupling partners. Mechanistic studies involving NMR, kinetics, and DFT calculations demonstrated that NOBINs are efficiently formed via radical–radical coupling, which is the cooperative coupling between a cation radical species from an electron donor–acceptor (EDA) complex of photoactivated 2-naphthylamines with singlet oxo-terminal O2and a radical species of 2-naphthols activated by a chiral vanadium catalyst. This work expands the scope of asymmetric transformations, enabling heterocoupling with various partners that are unreactive toward vanadium catalysts alone.

The full-text file will be made open to the public on 17 October 2026 in accordance with the publisher's policy.

103019

Enantioselective Heterocoupling of 2-Naphthylamines with 2-Naphthol Derivatives via Cooperative Photoactivation and Chiral Vanadium(V) Catalysis

American Chemical Society

英語

2025-10-17

ACS Catalysis

15

21

18077

18086

https://doi.org/10.1021/acscatal.5c05038

https://hdl.handle.net/11094/103019