Carbometallation chemistry
Editor: Prof. Ilan Marek
Technion – Israel Institute of Technology
Technion – Israel Institute of Technology
Following the pioneering Ziegler addition of nucleophiles to nonactivated unsaturated carbon–carbon bonds, the controlled carbometallation reaction has emerged. Since then, reactions that result in the addition of a carbon–metal bond of an organometallic across a carbon–carbon unsaturated system, leading to a new organometallic in which the newly formed carbon–metal bond can be used for further synthetic transformations, are called carbometallation reactions. In the past few decades, the intra- as well as intermolecular additions of various organometallic species to a large variety of alkynes, alkenes and allenes have been successfully reported.
Carbometallation chemistry
- Ilan Marek
Beilstein J. Org. Chem. 2013, 9, 234–235, doi:10.3762/bjoc.9.27
Stereoselective synthesis of tetrasubstituted alkenes via a sequential carbocupration and a new sulfur–lithium exchange
- Andreas Unsinn,
- Cora Dunst and
- Paul Knochel
Beilstein J. Org. Chem. 2012, 8, 2202–2206, doi:10.3762/bjoc.8.248
Highly stereocontrolled synthesis of trans-enediynes via carbocupration of fluoroalkylated diynes
- Tsutomu Konno,
- Misato Kishi and
- Takashi Ishihara
Beilstein J. Org. Chem. 2012, 8, 2207–2213, doi:10.3762/bjoc.8.249
Intramolecular carbolithiation of N-allyl-ynamides: an efficient entry to 1,4-dihydropyridines and pyridines – application to a formal synthesis of sarizotan
- Wafa Gati,
- Mohamed M. Rammah,
- Mohamed B. Rammah and
- Gwilherm Evano
Beilstein J. Org. Chem. 2012, 8, 2214–2222, doi:10.3762/bjoc.8.250
Radical zinc-atom-transfer-based carbozincation of haloalkynes with dialkylzincs
- Fabrice Chemla,
- Florian Dulong,
- Franck Ferreira and
- Alejandro Pérez-Luna
Beilstein J. Org. Chem. 2013, 9, 236–245, doi:10.3762/bjoc.9.28
Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation
- Kei Murakami and
- Hideki Yorimitsu
Beilstein J. Org. Chem. 2013, 9, 278–302, doi:10.3762/bjoc.9.34
Inter- and intramolecular enantioselective carbolithiation reactions
- Asier Gómez-SanJuan,
- Nuria Sotomayor and
- Esther Lete
Beilstein J. Org. Chem. 2013, 9, 313–322, doi:10.3762/bjoc.9.36
Regio- and stereoselective carbometallation reactions of N-alkynylamides and sulfonamides
- Yury Minko,
- Morgane Pasco,
- Helena Chechik and
- Ilan Marek
Beilstein J. Org. Chem. 2013, 9, 526–532, doi:10.3762/bjoc.9.57
Intramolecular carbolithiation cascades as a route to a highly strained carbocyclic framework: competition between 5-exo-trig ring closure and proton transfer
- William F. Bailey and
- Justin D. Fair
Beilstein J. Org. Chem. 2013, 9, 537–543, doi:10.3762/bjoc.9.59
Carbolithiation of N-alkenyl ureas and N-alkenyl carbamates
- Julien Lefranc,
- Alberto Minassi and
- Jonathan Clayden
Beilstein J. Org. Chem. 2013, 9, 628–632, doi:10.3762/bjoc.9.70
Intramolecular carbonickelation of alkenes
- Rudy Lhermet,
- Muriel Durandetti and
- Jacques Maddaluno
Beilstein J. Org. Chem. 2013, 9, 710–716, doi:10.3762/bjoc.9.81
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