Highly Stereoselective Synthesis of Imine-Containing Dibenzo[b,d]azepines by a Palladium(II)-Catalyzed [5+2] Oxidative Annulation of o-Arylanilines with Alkynes

Angewandte Chemie
Zhijun ZuoXinjun Luan

Abstract

A novel palladium(II)-catalyzed [5+2] oxidative annulation of readily available o-arylanilines with alkynes has been developed for building a seven-membered N-heterocyclic architecture containing a biaryl linkage. This method is applicable to a wide range of unprotected o-arylanilines and internal alkynes, and results in the chemoselective preparation of imine-containing dibenzo[b,d]azepines in high yields with excellent diastereoselectivity with respect to the two types of stereogenic elements.

References

Oct 20, 2005·Journal of the American Chemical Society·W C Peter TsangStephen L Buchwald
Feb 28, 2008·Journal of the American Chemical Society·Denise A ColbyJonathan A Ellman
Nov 13, 2008·Journal of the American Chemical Society·James A Jordan-HoreMatthew J Gaunt
Mar 14, 2009·Bioorganic & Medicinal Chemistry Letters·Stefano PegoraroStephan Grissmer
May 15, 2009·Chemical Reviews·Denise A ColbyJonathan A Ellman
Jun 26, 2009·Journal of the American Chemical Society·David R StuartKeith Fagnou
Aug 27, 2009·Journal of the American Chemical Society·Nicolas Guimond, Keith Fagnou
Apr 3, 2010·Journal of the American Chemical Society·Xiaodan ZhaoVy M Dong
May 4, 2010·Journal of the American Chemical Society·Nicolas GuimondKeith Fagnou
Jun 29, 2010·Journal of the American Chemical Society·Souvik RakshitFrank Glorius
Jul 29, 2010·Journal of the American Chemical Society·Todd K Hyster, Tomislav Rovis
Aug 27, 2010·Chemistry : a European Journal·Tetsuya Satoh, Masahiro Miura
Jun 15, 2011·Chemical Society Reviews·Joanna Wencel-DelordFrank Glorius
Dec 15, 2011·Accounts of Chemical Research·Keary M EngleJin-Quan Yu
Oct 12, 2012·Chemistry : a European Journal·Zunjun LiangYuhong Zhang
Jul 26, 2013·Organic Letters·Chiharu SuzukiMasahiro Miura
Nov 8, 2013·Journal of the American Chemical Society·Jiang NanYaoyu Wang
Dec 10, 2013·Journal of the American Chemical Society·Andrés SeoaneMoisés Gulías
Dec 25, 2013·Bioorganic & Medicinal Chemistry Letters·Raghavan RajagopalanParthasarathi Rajagopalan
May 14, 2014·Journal of the American Chemical Society·Andrés SeoaneMoisés Gulías
Dec 4, 2014·Organic Letters·Bing-Jie ZhangXiang-Hai Cai
Apr 7, 2015·Accounts of Chemical Research·Guoyong Song, Xingwei Li

❮ Previous
Next ❯

Citations

Feb 11, 2016·Organic Letters·Ya-Ping HanYong-Min Liang
Mar 28, 2017·Organic Letters·Borja CendónJosé L Mascareñas
Jan 1, 2017·Chemistry : a European Journal·Lucien D CaspersBoris J Nachtsheim
May 30, 2020·Chemical Communications : Chem Comm·Zeng GaoGaoxi Jiang
Apr 3, 2020·Chemistry : a European Journal·Naoto Chatani, Supriya Rej
Jul 27, 2020·Chemistry : a European Journal·Barry M TrostJohnathan E Schultz
Jul 9, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Prasanjit GhoshMahiuddin Baidya
Mar 10, 2018·The Journal of Organic Chemistry·Pratheepkumar AnnamalaiShih-Ching Chuang
Aug 27, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Sandeep KumarPralay Das
Dec 13, 2017·Organic Letters·Jingjing LiuXinjun Luan

❮ 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.