ortho-Alkynyl Benzyl Alcohols as C6 Synthons in Regioselective Construction of Polysubstituted Naphthalenes

Xuemei Wei; Tao Cai; Zhebing Zhang; Yanjuan Luo; Tianbo Shang; Hualiang Shen; Huiting Xu; Lemao Yu; Xiang Luo; Guoqi Yu; Runpu Shen

doi:10.1021/acs.joc.4c00491

ortho-Alkynyl Benzyl Alcohols as C6 Synthons in Regioselective Construction of Polysubstituted Naphthalenes

J Org Chem. 2024 May 13. doi: 10.1021/acs.joc.4c00491. Online ahead of print.

Authors

Xuemei Wei^{1

2}, Tao Cai^{1

2}, Zhebing Zhang¹, Yanjuan Luo^{1

2}, Tianbo Shang^{1

2}, Hualiang Shen^{1

2}, Huiting Xu^{1

2}, Lemao Yu¹, Xiang Luo¹, Guoqi Yu², Runpu Shen^{1

2}

Affiliations

¹ College of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing 312000, China.
² Zhejiang Engineering Research Center of Fat-Soluble Vitamin, Shaoxing University, Shaoxing312000, China.

PMID: 38738759
DOI: 10.1021/acs.joc.4c00491

Abstract

A straightforward methodology for the assembly of polysubstituted naphthalenes from ortho-alkynyl benzyl alcohols, enabled by using catalytic amounts of Tf₂O, has been developed. This transformation not only features transition-metal free and without using other bases and additives but also provides a new synthetic application for ortho-alkynyl benzyl alcohols, i.e., as C6 synthons for the construction of PAHs.