ChemInform Abstract: C-H Bond Formation with Boronic Acids and Derivatives by Transition-Metal-Free Conjugate Addition Reactions

ChemInform ◽  
2016 ◽  
Vol 47 (40) ◽  
Author(s):  
Francisco Sanchez-Sancho ◽  
Aurelio G. Csaky
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Conjugate Addition ◽  
Boronic Acids ◽  
Addition Reactions ◽  
Metal Free

scholarly journals Transition‐Metal‐Free Coupling of 1,3‐Dipoles and Boronic Acids as a Sustainable Approach to C−C Bond Formation

2020 ◽  
Vol 26 (46) ◽  
pp. 10591-10597
Author(s):  
Keith Livingstone ◽  
Sophie Bertrand ◽  
Alan R. Kennedy ◽  
Craig Jamieson
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Boronic Acids ◽  
Metal Free

scholarly journals Rate Dependence on Inductive and Resonance Effects for the Organocatalyzed Enantioselective Conjugate Addition of Alkenyl and Alkynyl Boronic Acids to β-Indolyl Enones and β-Pyrrolyl Enones

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1615
Author(s):  
Amy Boylan ◽  
Thien S. Nguyen ◽  
Brian J. Lundy ◽  
Jian-Yuan Li ◽  
Ravikrishna Vallakati ◽  
...  
Keyword(s):  
Positive Charge ◽  
Bond Formation ◽  
Conjugate Addition ◽  
Reaction Rates ◽  
Boronic Acids ◽  
Key Factors ◽  
Resonance Contribution ◽  
Reaction Conditions ◽  
Resonance Effects ◽  
Resonance Stabilization

Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the enone β-carbon, the faster the reaction. For the latter, greater resonance stabilization of the benzylic cationic charge accelerates the reaction. Thus, reaction rates are increased by the closer proximity of inductive electron-withdrawing elements, but if resonance effects are involved, then increased rates are observed with electron-donating ability. Evidence for these trends in isomeric substrates is presented, and the application of these insights has allowed for reaction conditions that provide improved reactivity with previously problematic substrates.

Visible light-mediated transition metal-free esterification of amides with boronic acids

2020 ◽  
Vol 61 (43) ◽  
pp. 152444
Author(s):  
Hao Ding ◽  
Wan-Ying Qi ◽  
Jing-Song Zhen ◽  
Qiuping Ding ◽  
Yong Luo
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Boronic Acids ◽  
Metal Free
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