Trifluoroacetic Anhydride Promoted Tandem Conjugate Addition of Boronic Acids/Acetal Ring Opening

2012 ◽  
Vol 14 (5) ◽  
pp. 1187-1189 ◽  
Author(s):  
Silvia Roscales ◽  
Aurelio G. Csákÿ
Keyword(s):  
Ring Opening ◽  
Conjugate Addition ◽  
Boronic Acids ◽  
Trifluoroacetic Anhydride ◽  
Acetal Ring

Trifluoroacetic anhydride—catalyzed conjugate addition of boronic acids to α,β-unsaturated ketones

2012 ◽  
Vol 53 (35) ◽  
pp. 4721-4724 ◽  
Author(s):  
Silvia Roscales ◽  
Ángela Rincón ◽  
Eduardo Buxaderas ◽  
Aurelio G. Csákÿ
Keyword(s):  
Conjugate Addition ◽  
Boronic Acids ◽  
Trifluoroacetic Anhydride ◽  
Unsaturated Ketones

ChemInform Abstract: Trifluoroacetic Anhydride-Catalyzed Conjugate Addition of Boronic Acids to α,β-Unsaturated Ketones.

ChemInform ◽  
2012 ◽  
Vol 43 (48) ◽  
pp. no-no
Author(s):  
Silvia Roscales ◽  
Angela Rincon ◽  
Eduardo Buxaderas ◽  
Aurelio G. Csaky
Keyword(s):  
Conjugate Addition ◽  
Boronic Acids ◽  
Trifluoroacetic Anhydride ◽  
Unsaturated Ketones

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.

scholarly journals Rh-Catalyzed Conjugate Addition of Aryl and Alkenyl Boronic Acids to α-Methylene-β-lactones: Stereoselective Synthesis of trans-3,4-Disubstituted β-Lactones

2017 ◽  
Vol 19 (17) ◽  
pp. 4460-4463 ◽  
Author(s):  
Christian A. Malapit ◽  
Irungu K. Luvaga ◽  
Donald R. Caldwell ◽  
Nicholas K. Schipper ◽  
Amy R. Howell
Keyword(s):  
Stereoselective Synthesis ◽  
Conjugate Addition ◽  
Boronic Acids

Chiral P-Containing Palladacycle-Catalyzed Asymmetric Ring-Opening Reactions of Oxabicyclic Alkenes with Alkenyl Boronic Acids

Synlett ◽  
2011 ◽  
Vol 2011 (07) ◽  
pp. 943-946 ◽  
Author(s):  
Xue-Long Hou ◽  
Xiao-Jun Huang ◽  
Dong-Liang Mo ◽  
Chang-Hua Ding
Keyword(s):  
Ring Opening ◽  
Boronic Acids ◽  
Ring Opening Reactions ◽  
Oxabicyclic Alkenes ◽  
Asymmetric Ring Opening

Transition-metal free reactions of boronic acids: cascade addition – ring-opening of furans towards functionalized γ-ketoaldehydes

2016 ◽  
Vol 52 (14) ◽  
pp. 3018-3021 ◽  
Author(s):  
S. Roscales ◽  
A. G. Csákÿ
Keyword(s):  
Transition Metal ◽  
Ring Opening ◽  
Boronic Acids ◽  
Metal Free

We describe the first ring-opening of furfuryl alcohols with boronic acids to afford functionalized γ-ketoaldehydes.

PdII-Catalyzed Conjugate Addition of Boronic Acids to Ketoglutaconic Esters toward the Synthesis of Functionalized Pyridazin-3(2H)-ones with Neuroprotective Activity

2012 ◽  
Vol 2012 (27) ◽  
pp. 5398-5405 ◽  
Author(s):  
Silvia Roscales ◽  
Andrea Ortega ◽  
Sagrario Martín-Aragón ◽  
Paloma Bermejo-Bescós ◽  
Aurelio G. Csákÿ
Keyword(s):  
Conjugate Addition ◽  
Boronic Acids ◽  
Neuroprotective Activity
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