Aromatization-Driven Cascade [1,5]-Hydride Transfer/Spirocyclization Promoted by Fluorinated Alcohols

Xintong Lv; Fangzhi Hu; Kang Duan; Shuai-Shuai Li; Qing Liu; Jian Xiao

doi:10.1021/acs.joc.8b02754

Aromatization-Driven Cascade [1,5]-Hydride Transfer/Spirocyclization Promoted by Fluorinated Alcohols

J Org Chem. 2019 Feb 15;84(4):1833-1844. doi: 10.1021/acs.joc.8b02754. Epub 2019 Jan 31.

Authors

Xintong Lv¹, Fangzhi Hu¹, Kang Duan¹, Shuai-Shuai Li¹, Qing Liu², Jian Xiao^{1

3}

Affiliations

¹ College of Chemistry and Pharmaceutical Sciences , Qingdao Agricultural University , Qingdao 266109 , China.
² College of Chemical and Environmental Engineering , Shandong University of Science and Technology , Qingdao 266590 , China.
³ College of Marine Science and Engineering , Qingdao Agricultural University , Qingdao 266109 , China.

PMID: 30608677
DOI: 10.1021/acs.joc.8b02754

Abstract

The aromatization-driven redox-neutral cascade [1,5]-hydride transfer/spirocyclization and cascade [1,5]-hydride transfer/hydrolysis from para-quinone methide in HFIP were developed. These protocols enabled the synthesis of azaspirocyclohexadienones and ortho-benzylated anilines in good to high yields under mild conditions, featuring room temperature, additive-free, and good functional group tolerance.