Ligand-Free Copper(I)-Catalyzed Benzylic Acyloxylation of 2-Alkylpyridines under Aerobic Conditions

The Journal of Organic Chemistry
Li ChengTuan-Jie Li

Abstract

A ligand-free copper(I)-catalyzed benzylic acyloxylation of 2-alkylpyridines with carboxylic acids was realized by using 1.0 atm of O2 as a green oxidant. The transformation provided a facile access to a wide range of N-heterocyclic esters through C-O bond formation, with broad substrate scope and good functional group tolerance. Preliminary mechanistic investigations showed that this protocol included a radical process.

References

Aug 5, 2004·Journal of the American Chemical Society·Lopa V DesaiMelanie S Sanford
Aug 12, 2005·Organic Letters·Dmitry Shabashov, Olafs Daugulis
Jan 19, 2010·Chemical Reviews·Thomas W Lyons, Melanie S Sanford
Feb 10, 2010·Chemistry : a European Journal·Rodolphe JazzarOlivier Baudoin
Aug 26, 2010·Chemical Communications : Chem Comm·Huanfeng JiangXiaohang Liu
Sep 10, 2010·Chemistry : a European Journal·Matthew D Hill
Oct 29, 2011·Angewandte Chemie·Alison E WendlandtShannon S Stahl
Feb 24, 2012·Chemical Society Reviews·Zhuangzhi ShiNing Jiao
Jul 7, 2012·Organic Letters·Raja K RitAkhila K Sahoo
Sep 13, 2012·Chemical Communications : Chem Comm·Juan HuangBin Wang
Oct 11, 2013·The Journal of Organic Chemistry·Long JuYuhong Zhang
Jan 1, 2014·Organic Letters·Lihong Zhou, Wenjun Lu
Jul 26, 2014·Chemistry, an Asian Journal·Xuesong WuHaibo Ge
Sep 3, 2014·Organic Letters·Zhen WangMotomu Kanai
Nov 13, 2014·Journal of the American Chemical Society·Ba L TranJohn F Hartwig
Dec 23, 2014·Chemical Reviews·Xun-Xiang GuoWanbin Zhang
Jan 22, 2015·Chemical Communications : Chem Comm·Meining WangAo Zhang
Mar 24, 2016·Angewandte Chemie·Zhongxing HuangGuangbin Dong
Apr 14, 2016·Chemical Society Reviews·T GenschJ Wencel-Delord
Aug 5, 2016·Organic & Biomolecular Chemistry·Ganesh MajjiBhisma K Patel
Jan 5, 2017·Chemical Reviews·Yoonsu ParkSukbok Chang
Feb 9, 2017·Journal of the American Chemical Society·Qi-Liang YangTian-Sheng Mei
Jul 13, 2017·Chemical Reviews·Jian HeJin-Quan Yu
Aug 29, 2017·The Journal of Organic Chemistry·Dnyaneshwar N Garad, Santosh B Mhaske
Jan 30, 2018·The Journal of Organic Chemistry·Yong ZhengLijiang Xuan
Apr 21, 2018·Chemical Science·Yan Xu, Guangbin Dong
Jul 24, 2018·Chemical Society Reviews·Carlo SambiagioMichael Schnürch
Sep 1, 2018·Chemical Communications : Chem Comm·Min-Hua HuangBo Jiang
Sep 6, 2018·Accounts of Chemical Research·Fei WangGuosheng Liu
Sep 22, 2018·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Ashish A MishraBhalchandra M Bhanage

❮ Previous
Next ❯

Citations

Jan 9, 2020·Organic & Biomolecular Chemistry·Milanpreet Kaur, Jeffrey F Van Humbeck
Sep 29, 2021·The Journal of Organic Chemistry·Wenrong WangTuan-Jie Li

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.