Synlett 2023; 34(09): 1042-1048
DOI: 10.1055/a-2005-5372
letter

Addition of Alcohols onto Electron-Deficient Heteroarenium Salts: A Reversible Covalent Bonding Process under Basic Conditions

Baoli Chen
a   State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen, 518055, P. R. of China
,
En Li
c   Pingshan Translational Medicine Center, Shenzhen Bay Laboratory, Shenzhen, 518055, P. R. of China
,
Feifei Song
a   State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen, 518055, P. R. of China
,
Nicolas Guimond
d   Process Research, Bayer AG Crop Science, 40789 Monheim, Germany
,
Jiean Chen
a   State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen, 518055, P. R. of China
c   Pingshan Translational Medicine Center, Shenzhen Bay Laboratory, Shenzhen, 518055, P. R. of China
,
Yong Huang
b   Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Hong Kong SAR, P. R. of China
› Author Affiliations
This work was financially supported by the National Natural Science Foundation of China (21825101), Hong Kong RGC (16300320), Guangdong Basic and Applied Basic Research Foundation (2019A1515011641) and Shenzhen Science and Technology Innovation Commission (SGDX2019081623241924, KCXFZ20201221173404013).


Abstract

The reversible addition of benzyl alcohol onto heteroarenium salts under basic conditions was studied. Fine-tuning of the nature of the arenium and substituents allowed the discovery of a range of pyrimidinium substrates that can undergo C6-selective alcohol addition. Crossover experiments were also performed to confirm the addition-elimination equilibrium under basic conditions.

Supporting Information



Publication History

Received: 07 September 2022

Accepted after revision: 02 January 2023

Accepted Manuscript online:
02 January 2023

Article published online:
25 January 2023

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