Direct C(sp(2) )-C(sp(3) ) Cross-Coupling of Diaryl Zinc Reagents with Benzylic, Primary, Secondary, and Tertiary Alkyl Halides

Angewandte Chemie
Jay J DunsfordMichael J Ingleson

Abstract

The direct C(sp(2) )-C(sp(3) ) cross-coupling of diaryl zinc reagents with benzylic, primary, secondary, and tertiary alkyl halides proceeded in the absence of coordinating ethereal solvents at ambient temperature without the addition of a catalyst. The C(sp(2) )-C(sp(3) ) cross-coupling showed excellent functional-group tolerance, and products were isolated in high yields, generally without the requirement for purification by chromatography. This process represents an expedient, operationally simple method for the construction of new C(sp(2) )-C(sp(3) ) bonds.

References

Nov 15, 2002·Journal of the American Chemical Society·Alois FürstnerHelga Krause
Feb 3, 2005·Journal of the American Chemical Society·Jens RudolphPer-Ola Norrby
Jul 2, 2005·Angewandte Chemie·K C NicolaouDavid Sarlah
Jul 31, 2007·Journal of the American Chemical Society·Takuji Hatakeyama, Masaharu Nakamura
Jan 29, 2009·Angewandte Chemie·Alena Rudolph, Mark Lautens
Oct 21, 2009·Chemical Communications : Chem Comm·Robin B BedfordMark C Wilkinson
Mar 10, 2010·Proceedings of the National Academy of Sciences of the United States of America·Eva HeviaMatthew D McCall
May 25, 2010·The Journal of Organic Chemistry·Dipankar SrimaniAmitabha Sarkar
Aug 12, 2010·Journal of the American Chemical Society·Pamela M Lundin, Gregory C Fu
Sep 24, 2010·Nature Chemistry·Jian-Rong Li, Hong-Cai Zhou
Jan 6, 2012·Chemical Society Reviews·Isabelle ThoméCarsten Bolm
Jun 12, 2012·Angewandte Chemie·Lucas C McCannMichael G Organ
Jun 15, 2012·Journal of the American Chemical Society·Christopher J AdamsJoshua Nunn
Dec 12, 2012·Angewandte Chemie·Robin B BedfordJoshua Nunn
Jan 4, 2013·Journal of the American Chemical Society·Susan L Zultanski, Gregory C Fu
Jul 25, 2013·Nature Chemistry·Massimo GianneriniBen L Feringa
Aug 21, 2013·Journal of the American Chemical Society·Soumik Biswas, Daniel J Weix
Apr 1, 2014·Journal of the American Chemical Society·Yufan Liang, Gregory C Fu
Jun 21, 2014·Nature Chemistry·Amadeu BonetVarinder K Aggarwal

❮ Previous
Next ❯

Citations

Feb 26, 2016·The Journal of Organic Chemistry·Santiago BarrosoPaul Knochel
Sep 2, 2015·Journal of the American Chemical Society·Xuan WangHegui Gong
Nov 12, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Jay J DunsfordMichael J Ingleson
Sep 30, 2017·Chemistry : a European Journal·Richard J ProcterMichael J Ingleson
Jan 26, 2016·Chemical Communications : Chem Comm·Andreas D BenischkePaul Knochel
Sep 30, 2017·Chemistry, an Asian Journal·Wei-Can Dai, Zhong-Xia Wang
Jan 7, 2016·Beilstein Journal of Organic Chemistry·Bijay Shrestha, Ramesh Giri
Jul 28, 2016·Chemistry : a European Journal·Daniel L CrossleyMichael J Ingleson
Jan 23, 2018·Organic & Biomolecular Chemistry·Wen-Jing Pan, Zhong-Xia Wang
Aug 24, 2017·Chemistry, an Asian Journal·Dong-Yu WangMasanobu Uchiyama
Aug 29, 2019·Chemical Communications : Chem Comm·Matthew M MorganBenjamin S Gelfand
May 24, 2019·The Journal of Organic Chemistry·Nivedita S MahajaniJohn D Chisholm
Dec 29, 2020·Journal of the American Chemical Society·Peng GuoXing-Zhong Shu
Oct 9, 2018·Journal of the American Chemical Society·Xuan WangHegui Gong

❮ 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.