Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds

Chemical Science
Joseph DerosaKeary M Engle

Abstract

A nickel-catalyzed conjunctive cross-coupling of non-conjugated alkenes, alkyl halides, and alkylzinc reagents is reported. Regioselectivity is controlled by chelation of a removable bidentate 8-aminoquinoline directing group. Under optimized conditions, a wide range of 1,2-dialkylated products can be accessed in moderate to excellent yields. To the best of our knowledge, this report represents the first example of three-component 1,2-dialkylation of non-conjugated alkenes to introduce differentiated alkyl fragments.

References

Jan 5, 2002·The Journal of Organic Chemistry·Tai-Hsiang HuangChien-Hong Cheng
Jan 20, 2005·Angewandte Chemie·Anja C Frisch, Matthias Beller
Sep 22, 2005·Journal of the American Chemical Society·Vladimir G ZaitsevOlafs Daugulis
Jan 31, 2007·Journal of the American Chemical Society·Hegui GongMichel R Gagné
Jan 29, 2009·Angewandte Chemie·Alena Rudolph, Mark Lautens
Oct 16, 2009·Journal of Medicinal Chemistry·Frank LoveringChristine Humblet
May 11, 2012·Angewandte Chemie·Carin C C Johansson SeechurnVictor Snieckus
Jan 1, 2014·Journal of the American Chemical Society·Yoshinori Aihara, Naoto Chatani
May 16, 2014·Nature·Sarah Z TaskerTimothy F Jamison
Mar 11, 2015·Accounts of Chemical Research·Olafs DaugulisLy Dieu Tran
Oct 26, 2016·Journal of the American Chemical Society·Zhen LiuKeary M Engle
May 11, 2017·Journal of the American Chemical Society·Andrés García-DomínguezCristina Nevado
Jul 25, 2017·Journal of the American Chemical Society·Joseph DerosaKeary M Engle
Oct 4, 2017·Journal of the American Chemical Society·Miriam L O'DuillKeary M Engle
Nov 9, 2017·Journal of the American Chemical Society·Gabriel J Lovinger, James P Morken
Mar 9, 2018·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Roshan K DhunganaRamesh Giri

❮ Previous
Next ❯

Citations

Feb 12, 2019·Angewandte Chemie·Wang WangGuoyin Yin
Apr 3, 2019·Chemical Communications : Chem Comm·Jianjun WangTatiana Besset
May 6, 2019·Angewandte Chemie·Yangyang LiGuoyin Yin
Jan 21, 2020·Angewandte Chemie·Van T TranKeary M Engle
Dec 5, 2019·Angewandte Chemie·Yuqiang LiGuoyin Yin
May 22, 2020·Angewandte Chemie·Ting LiuCongyang Wang
Mar 20, 2019·Angewandte Chemie·Youxiang Jin, Chuan Wang
Jul 8, 2020·Angewandte Chemie·Songlin ZhengWeiming Yuan
Mar 8, 2019·Chemical Science·Youxiang Jin, Chuan Wang
Jan 27, 2021·Chemical Communications : Chem Comm·Ying-Qiong GuoXing-Guo Zhang
Aug 13, 2021·Accounts of Chemical Research·Laura M Wickham, Ramesh Giri
Sep 21, 2018·Journal of the American Chemical Society·Kuai WangWangqing Kong
Aug 23, 2019·Journal of the American Chemical Society·Wei ShuCristina Nevado
Nov 14, 2018·Journal of the American Chemical Society·Chunlin TangXihe Bi
Dec 4, 2020·Journal of the American Chemical Society·Roshan K DhunganaRamesh Giri
Mar 24, 2020·Organic Letters·Youxiang JinChuan Wang
Jan 24, 2020·Journal of the American Chemical Society·Pei FanChuan Wang
Jul 1, 2020·Journal of the American Chemical Society·Xiaofeng WeiCristina Nevado
Aug 16, 2019·Organic Process Research & Development·Evan C BornowskiJohn P Wolfe
Mar 19, 2021·ACS Catalysis·Xiaoxu Qi, Tianning Diao
Aug 27, 2019·Journal of the American Chemical Society·Takuya IshiiHirohisa Ohmiya
Dec 12, 2018·Journal of the American Chemical Society·Joseph DerosaKeary M Engle
May 11, 2019·Organic Letters·Wang WangGuoyin Yin

❮ 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.