Visible-Light-Induced ortho-Quinone Methides Formation in Situ Using ortho-Alkylarenols as Precursors for Tandem [4 + 2] Cycloaddition Reaction

Shu Wang; Ge Liang; Cheng Wang; Chen-Hong Wang; Zhiyuan Huang; Chen-Ho Tung; Li-Zhu Wu

doi:10.1021/acs.orglett.4c04494

Visible-Light-Induced ortho-Quinone Methides Formation in Situ Using ortho-Alkylarenols as Precursors for Tandem [4 + 2] Cycloaddition Reaction

Org Lett. 2024 Dec 26. doi: 10.1021/acs.orglett.4c04494. Online ahead of print.

Authors

Shu Wang^{1

2}, Ge Liang^{1

2}, Cheng Wang^{1

2}, Chen-Hong Wang^{1

2}, Zhiyuan Huang^{1

2}, Chen-Ho Tung^{1

2}, Li-Zhu Wu^{1

2}

Affiliations

¹ Key Laboratory of Photochemical Conversion and Optoelectronic Materials, New Cornerstone Science Laboratory, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, P. R. China.
² School of Future Technology, University of Chinese Academy of Sciences, Beijing 100049, P. R. China.

PMID: 39723814
DOI: 10.1021/acs.orglett.4c04494

Abstract

Reported herein is the generation of ortho-quinone methides (o-QMs) via metal-free visible-light-induced oxidation of ortho-alkylarenols, as well as their subsequent reaction with olefins to afford chromans in good to excellent yields (up to 91%). The key is the selective activation of the benzylic C(sp³)-H bond of ortho-alkylarenols via single electron transfer (SET) and the formation of o-QMs via hydrogen atom transfer (HAT).