Chemodivergent Synthesis of One-Carbon-Extended Alcohols via Copper-Catalyzed Hydroxymethylation of Alkynes with Formic Acid

The development of selective catalytic reactions that utilize easily available reagents for the efficient synthesis of alcohols is a long-standing goal of chemical research. Here an intriguing strategy for the chemodivergent copper-catalyzed hydroxymethylation of alkynes with formic acid and hydrosi...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2021-07, Vol.23 (13), p.4997-5001
Main Authors: Jin, Xin, Fu, Hong-Chen, Wang, Mei-Yan, Huang, Shouying, Wang, Yue, He, Liang-Nian, Ma, Xinbin
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The development of selective catalytic reactions that utilize easily available reagents for the efficient synthesis of alcohols is a long-standing goal of chemical research. Here an intriguing strategy for the chemodivergent copper-catalyzed hydroxymethylation of alkynes with formic acid and hydrosilane has been developed. By simply tuning the amount of formic acid and reaction temperature, distinct one-carbon-extended primary alcohols, that is, allylic alcohols and β-branched alkyl alcohols, were produced with high levels of Z/E-, regio-, and enantioselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01473