Stoichiometric Photochemical Carbene Transfer by Bamford-Stevens Reaction

Chemistry : a European Journal
Sripati JanaRene M Koenigs


The photolysis of diazoalkanes is a timely strategy to conduct carbene-transfer reactions under mild and metal-free reaction conditions, and has developed as an important alternative to conventional metal-catalyzed carbene-transfer reactions. One of the major limitations lies within the rapidly occurring side reaction of the carbene intermediate with remaining diazoalkane molecules that result in the use of an excess of the reaction partner and thus impacts on the reaction efficiency. Herein, we describe a protocol that takes advantage of the in situ generation of donor-acceptor diazoalkanes by Bamford-Stevens reaction. Following this strategy, the concentration of the diazoalkane reaction partner can be minimized to reduce unwanted side reactions and to now conduct photochemical carbene transfer reactions under stoichiometric reaction conditions. We have explored this approach in the C-H and N-H functionalization and cyclopropanation reaction of N-heterocycles and could demonstrate the applicability of this method in 51 examples.


Jun 25, 2004·Chemical Communications : Chem Comm·Yajun Wang, Frank Caruso
Jan 25, 2008·Nature·Huw M L Davies, James R Manning
Sep 30, 2009·Chemical Reviews·Michael P DoyleLei Zhou
Jul 2, 2010·Organic & Biomolecular Chemistry·Georgiy B Shul'pin
Aug 12, 2010·Journal of the American Chemical Society·Yvette S Mimieux VaskeWilliam J McDonald
Jul 26, 2011·Chemical Society Reviews·Zhihui Shao, Hongbin Zhang
Mar 26, 2013·Chemical Society Reviews·Bin Li, Pierre H Dixneuf
Sep 4, 2014·Chemical Reviews·Chang-Liang Sun, Zhang-Jie Shi
Aug 19, 2015·Chemical Reviews·Alan FordM Anthony McKervey
Apr 14, 2016·Chemical Society Reviews·T GenschJ Wencel-Delord
Jun 17, 2016·Angewandte Chemie·Minqiang Jia, Shengming Ma
Mar 16, 2017·Angewandte Chemie·Vanessa ArredondoDavid L Van Vranken
Mar 30, 2017·Chemical Society Reviews·Ying Xia, Jianbo Wang
Apr 6, 2017·Chemical Reviews·Rui ShangEiichi Nakamura
Jun 3, 2017·Chemical Communications : Chem Comm·Katharina J HockRene M Koenigs
Jul 22, 2017·Organic & Biomolecular Chemistry·Pavel K Mykhailiuk
Feb 2, 2018·Nature·Zhaofeng WangMarcos G Suero
Jun 26, 2018·Chemical Science·Igor D Jurberg, Huw M L Davies
Jul 25, 2018·Chemical Communications : Chem Comm·Tiebo XiaoLei Zhou
Nov 28, 2018·Angewandte Chemie·Renè HommelsheimRene M Koenigs
Dec 14, 2018·Organic & Biomolecular Chemistry·Łukasz W CiszewskiDorota Gryko
Mar 29, 2019·Chemistry : a European Journal·Zhen YangRene M Koenigs
Apr 9, 2019·Chemical Communications : Chem Comm·Feifei He, Rene M Koenigs
Jul 2, 2019·Chemical Communications : Chem Comm·Zhen YangRene M Koenigs
Aug 3, 2019·The Journal of Organic Chemistry·Claire EmpelRene M Koenigs
Aug 16, 2019·Chemistry : a European Journal·Pavel K Mykhailiuk, Rene M Koenigs
Dec 6, 2019·Chemical Science·Ziyan ZhangVladimir Gevorgyan

❮ Previous
Next ❯

Related Concepts

Trending Feeds


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.

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.

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.

Epigenetics Insights from Twin Studies

Find the latest research on epigenetics and twin studies 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.


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.

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.

Regulation of Vocal-Motor Plasticity

Dopaminergic projections to the basal ganglia and nucleus accumbens shape the learning and plasticity of motivated behaviors across species including the regulation of vocal-motor plasticity and performance in songbirds. Discover the latest research on the regulation of vocal-motor plasticity here.

Myocardial Stunning

Myocardial stunning is a mechanical dysfunction that persists after reperfusion of previously ischemic tissue in the absence of irreversible damage including myocardial necrosis. Here is the latest research.