Main group organometallics in organic synthesis

1999 ◽  
pp. 2025-2046 ◽  
Author(s):  
Kamyar Afarinkia
Keyword(s):  
Organic Synthesis ◽  
Main Group

Activation of C–F, Si–F, and S–F Bonds by N-Heterocyclic Carbenes and Their Isoelectronic Analogues

Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1349-1360 ◽  
Author(s):  
Eunsung Lee ◽  
Ewa Pietrasiak
Keyword(s):  
Nucleophilic Substitution ◽  
Organic Synthesis ◽  
Bond Activation ◽  
Bond Cleavage ◽  
Oxidative Addition ◽  
Main Group ◽  
Heterocyclic Carbenes ◽  
Full Potential ◽  
Short Summary ◽  
Special Case

Reactions involving C–F, Si–F, and S–F bond cleavage with N-heterocyclic carbenes and isoelectronic species are reviewed. Most examples involve activation of aromatic C–F bond via an SNAr pathway and nucleophilic substitution of fluorine in electron-deficient olefins. The mechanism of the C–F bond activation depends on the reaction partners and the reaction can proceed via addition–elimination, oxidative addition (concerted or stepwise) or metathesis. The adducts formed upon substitution find applications in organic synthesis, as ligands and as stable radical precursors, but in most cases, their full potential remains unexplored.1 Introduction1.1 The C–F Bond1.2 C–F Bond Activation: A Short Summary1.3 C–F Bond Activation: A Special Case of SNAr1.4 N-Heterocyclic Carbenes (NHCs)1.5 The Purpose of this Article2 C–F bond Activation in Acyl Fluorides3 Activation of Vinylic C–F Bonds4 Activation of Aromatic C–F Bonds5 X–F Bond Activation (X = S or Si)6 C–F Bond Activation by Main Group Compounds Isoelectronic with NHCs7 Conclusions and Outlook

ChemInform Abstract: Functionalized Main-Group Organometallics for Organic Synthesis

ChemInform ◽  
2010 ◽  
Vol 33 (43) ◽  
pp. no-no
Author(s):  
Paul Knochel ◽  
Eike Hupe ◽  
Wolfgang Dohle ◽  
David M. Lindsay ◽  
Veronique Bonnet ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Main Group

Sterically Unprotected Nucleophilic Boron Cluster Reagents

2019 ◽  
Author(s):  
Xin Mu ◽  
Jonathan C. Axtell ◽  
Nicholas Bernier ◽  
Kent Kirlikovali ◽  
Dahee Jung ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Organic Synthesis ◽  
Substitution Reaction ◽  
Main Group ◽  
Cluster Anion ◽  
Nucleophilic Substitution Reaction ◽  
Boron Cluster

Herein, we demonstrate that the bench stable <i>closo</i>-hexaborate cluster anion can engage in a nucleophilic substitution reaction with a wide array of organic and main group electrophiles. The resulting molecules containing B‒C bonds can be further converted to tricoordinate boron species widely used in organic synthesis.<br>

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