Cobalt-catalysed site-selective intra- and intermolecular dehydrogenative amination of unactivated sp(3) carbons

Nature Communications
Xuesong WuHaibo Ge

Abstract

Cobalt-catalysed sp(2) C-H bond functionalization has attracted considerable attention in recent years because of the low cost of cobalt complexes and interesting modes of action in the process. In comparison, much less efforts have been devoted to the sp(3) carbons. Here we report the cobalt-catalysed site-selective dehydrogenative cyclization of aliphatic amides via a C-H bond functionalization process on unactivated sp(3) carbons with the assistance of a bidentate directing group. This method provides a straightforward synthesis of monocyclic and spiro β- or γ-lactams with good to excellent stereoselectivity and functional group tolerance. In addition, a new procedure has been developed to selectively remove the directing group, which enables the synthesis of free β- or γ-lactam compounds. Furthermore, the first cobalt-catalysed intermolecular dehydrogenative amination of unactivated sp(3) carbons is also realized.

References

Nov 8, 2007·Journal of the American Chemical Society·Andrew D Bolig, Maurice Brookhart
May 15, 2009·Chemical Reviews·Denise A ColbyJonathan A Ellman
Jun 26, 2009·Accounts of Chemical Research·Olafs DaugulisDmitry Shabashov
Jul 23, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Youcef BoutadlaAmalia I Poblador-Bahamonde
Jan 19, 2010·Chemical Reviews·Thomas W Lyons, Melanie S Sanford
Feb 10, 2010·Chemistry : a European Journal·Rodolphe JazzarOlivier Baudoin
May 8, 2010·Chemical Communications : Chem Comm·Florence ColletPhilippe Dauban
Aug 18, 2010·Journal of the American Chemical Society·Ke GaoNaohiko Yoshikai
Aug 26, 2010·Organic Letters·Zhenhua Ding, Naohiko Yoshikai
Nov 23, 2010·Chemical Society Reviews·Hongjian Lu, X Peter Zhang
Dec 17, 2010·Journal of the American Chemical Society·Quan ChenEiichi Nakamura
Feb 8, 2011·Chemical Society Reviews·Will R Gutekunst, Phil S Baran
Feb 22, 2011·Chemical Society Reviews·John F Hartwig
Mar 11, 2011·Chemical Society Reviews·Huw M L DaviesJin-Quan Yu
Aug 4, 2011·Angewandte Chemie·Jun PanStephen L Buchwald
Oct 1, 2011·Journal of the American Chemical Society·Pin-Sheng LeeNaohiko Yoshikai
Feb 3, 2012·Angewandte Chemie·Alvaro IglesiasKilian Muñiz
Feb 22, 2012·Science·M Christina White
Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
Mar 2, 2013·Chemical Communications : Chem Comm·Richard A LewisTrevor W Hayton
Mar 28, 2013·The Journal of Antibiotics·Kapil Tahlan, Susan E Jensen
Jun 14, 2013·Journal of the American Chemical Society·Ke Gao, Naohiko Yoshikai
Jun 20, 2013·Chemistry : a European Journal·Thomas W Lyons, Maurice Brookhart
Jun 22, 2013·Nature Chemistry·Karl D Collins, Frank Glorius
Jan 1, 2014·Journal of the American Chemical Society·Yoshinori Aihara, Naoto Chatani
Jan 30, 2014·Organic & Biomolecular Chemistry·Long-Wu YeFabien Gagosz
Mar 1, 2014·Accounts of Chemical Research·Ke Gao, Naohiko Yoshikai
Mar 22, 2014·Journal of the American Chemical Society·Hideya IkemotoMotomu Kanai
May 9, 2014·The Journal of Organic Chemistry·Nuancheng WangBaiquan Wang

❮ Previous
Next ❯

Citations

Feb 9, 2016·Journal of the American Chemical Society·Wei-Jun KongJin-Quan Yu
Feb 11, 2016·Organic Letters·Vinod G LandgeEkambaram Balaraman
Mar 2, 2016·Organic Letters·Lin-Bao ZhangMao-Ping Song
Sep 22, 2015·Journal of the American Chemical Society·Jitan ZhangYuhong Zhang
Jun 9, 2016·The Journal of Organic Chemistry·Ganesh PandeyDeepak Singh
Jun 18, 2016·The Journal of Organic Chemistry·Sourav Kumar SantraBhisma K Patel
Oct 5, 2016·Organic Letters·Vinod G LandgeEkambaram Balaraman
Oct 28, 2016·The Journal of Organic Chemistry·Yanrong LiHongjian Lu
Jan 5, 2017·Chemical Reviews·Yoonsu ParkSukbok Chang
Jan 26, 2017·The Journal of Organic Chemistry·Zheng-Yang GuShun-Jun Ji
Mar 17, 2017·Journal of the American Chemical Society·Bidraha BaghJarl Ivar van der Vlugt
Jun 8, 2017·Chemistry : a European Journal·Gerit PototschnigMichael Schnürch
Jul 28, 2016·Angewandte Chemie·Guangying TanJingsong You
Jun 4, 2016·Chemistry : a European Journal·Conghui TangNing Jiao
May 30, 2017·Chemical Science·Patrick WilliamsonMatthew J Gaunt
Apr 30, 2017·Chemical Science·Nagaraju BarsuBasker Sundararaju
Aug 24, 2016·Chemical Communications : Chem Comm·Zhongxue FangTiandi Tang
Jun 22, 2017·The Journal of Organic Chemistry·Desaboini Nageswar RaoParthasarathi Das
Jul 23, 2016·Chemical Communications : Chem Comm·Takuma YamaguchiNaoto Chatani
Nov 15, 2016·Organic & Biomolecular Chemistry·Liang HuGangguo Zhu
Jul 19, 2018·Organic & Biomolecular Chemistry·Ze-Lin LiChun Cai
Oct 29, 2017·Angewandte Chemie·Peng Wen TanJayasree Seayad
Sep 22, 2018·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Ashish A MishraBhalchandra M Bhanage
Oct 4, 2018·Chemical Communications : Chem Comm·Vanaparthi SatheeshTharmalingam Punniyamurthy
Jun 20, 2018·Chemistry : a European Journal·Nicolas SauermannLutz Ackermann

❮ Previous
Next ❯

Methods Mentioned

BETA
hydroacylation
amidation

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.