scholarly journals Mechanistic Investigation of the Nickel-Catalyzed Suzuki Reaction of N,O-Acetals: Evidence for Boronic Acid Assisted Oxidative Addition and an Iminium Activation Pathway

2012 ◽  
Vol 134 (41) ◽  
pp. 16967-16970 ◽  
Author(s):  
Kevin T. Sylvester ◽  
Kevin Wu ◽  
Abigail G. Doyle
Keyword(s):  
Boronic Acid ◽  
Suzuki Reaction ◽  
Oxidative Addition ◽  
Activation Pathway ◽  
Mechanistic Investigation

A Mechanistic Investigation of the Oxidative Addition of Alkyl Halides to Palladium Atoms

1977 ◽  
Vol 137 (1) ◽  
pp. 113-130 ◽  
Author(s):  
Kenneth J. Klabunde ◽  
John S. Roberts
Keyword(s):  
Oxidative Addition ◽  
Alkyl Halides ◽  
Mechanistic Investigation

Oxidative Addition of Haloalkanes to Metal Centers: A Mechanistic Investigation

2014 ◽  
Vol 33 (13) ◽  
pp. 3591-3595 ◽  
Author(s):  
Veeranna Yempally ◽  
Salvador Moncho ◽  
Sohail Muhammad ◽  
Edward N. Brothers ◽  
Bruce A. Arndtsen ◽  
...  
Keyword(s):  
Oxidative Addition ◽  
Metal Centers ◽  
Mechanistic Investigation

scholarly journals DABN Borazabicycles: Formation from MIDA Boronates and Synthetic Utility

2020 ◽  
Author(s):  
Sherif James Kaldas ◽  
chieh-hung tien ◽  
Gabriel dos Passos Gomes ◽  
Stephanie Meyer ◽  
martynas sirvinskas ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Transition State ◽  
Oxidative Addition ◽  
Mechanistic Investigation ◽  
Synthetic Utility

<div> <div> <div> <p>We report that coordinative hemilability allows the MIDA amine to behave as a nucleophile to intercept π-allyl intermediates. A mechanistic investigation indicates that this rearrangement proceeds through an SN2-like displacement at tetrasubstituted boron to furnish novel DABN (2,8- dioxa-5-aza-1-borabicyclo[3.3.1]nonane-3,7-dione) boronates. Oxidative addition into the N-C bond of the DABN scaffold reverses the reaction and furnishes borylated π-allyl intermediates that can then be trapped with complete linear selectivity. DFT calculations indicate that stabilizing interactions in the transition state, as well as the steric bulk of the MIDA unit, are the origins of the excellent regioselectivity. We further demonstrate the utility of our new reagents by way of a 3-component coupling that features allylammonium DABN boronates as linchpin reagents. This report disseminates a previously unknown aspect of MIDA boronates that can now be exploited. </p> </div> </div> </div>

scholarly journals DABN Borazabicycles: Formation from MIDA Boronates and Synthetic Utility

2020 ◽  
Author(s):  
Sherif James Kaldas ◽  
chieh-hung tien ◽  
Gabriel dos Passos Gomes ◽  
Stephanie Meyer ◽  
martynas sirvinskas ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Transition State ◽  
Oxidative Addition ◽  
Mechanistic Investigation ◽  
Synthetic Utility

<div> <div> <div> <p>We report that coordinative hemilability allows the MIDA amine to behave as a nucleophile to intercept π-allyl intermediates. A mechanistic investigation indicates that this rearrangement proceeds through an SN2-like displacement at tetrasubstituted boron to furnish novel DABN (2,8- dioxa-5-aza-1-borabicyclo[3.3.1]nonane-3,7-dione) boronates. Oxidative addition into the N-C bond of the DABN scaffold reverses the reaction and furnishes borylated π-allyl intermediates that can then be trapped with complete linear selectivity. DFT calculations indicate that stabilizing interactions in the transition state, as well as the steric bulk of the MIDA unit, are the origins of the excellent regioselectivity. We further demonstrate the utility of our new reagents by way of a 3-component coupling that features allylammonium DABN boronates as linchpin reagents. This report disseminates a previously unknown aspect of MIDA boronates that can now be exploited. </p> </div> </div> </div>

scholarly journals Synthetic and Mechanistic Investigation of an Oxime Ether Electrocyclization Approach to Heteroaromatic Boronic Acid Derivatives

2018 ◽  
Vol 24 (38) ◽  
pp. 9530-9534 ◽  
Author(s):  
Helena Mora-Radó ◽  
Lia Sotorríos ◽  
Matthew P. Ball-Jones ◽  
Laurent Bialy ◽  
Werngard Czechtizky ◽  
...  
Keyword(s):  
Boronic Acid ◽  
Oxime Ether ◽  
Mechanistic Investigation ◽  
Boronic Acid Derivatives

Mechanistic investigation of the oxidative addition reactions between different iridium (I) cyclooctadiene ([Ir(LL′)(cod)]) complexes and iodomethane

2005 ◽  
Vol 358 (8) ◽  
pp. 2457-2463 ◽  
Author(s):  
Melanie Theron ◽  
Ebeth Grobbelaar ◽  
Walter Purcell ◽  
Stephen S. Basson
Keyword(s):  
Oxidative Addition ◽  
Addition Reactions ◽  
Mechanistic Investigation

scholarly journals A Novel Synthetic Route of Fused Tricyclic Framework Quinoline Derivatives from Readily Available Aliphatic Amino Carboxylic Acid Substrates

2019 ◽  
Vol 35 (2) ◽  
pp. 611-617 ◽  
Author(s):  
Shireen Mohammed
Keyword(s):  
Carboxylic Acid ◽  
Boronic Acid ◽  
Suzuki Reaction ◽  
Main Reaction ◽  
Quinoline Derivatives ◽  
Synthetic Route ◽  
Amino Carboxylic Acid ◽  
High Yields ◽  
Reaction Processes ◽  
Acid Substrate

A novel and an efficient strategy of fused tricyclic quinoline heterocycle compounds from aliphatic amino carboxylic acid substrates is disclosed. The protocol here is proceed over main reaction processes including: cyclization, protection, amidine formation, further cyclization and finally coupling with boronic acid substrate through Suzuki reaction. These reactions afforded the corresponding products in high yields. Furthermore, all synthesized compounds were identified by spectral data.

A Mechanistic Investigation of Oxidative Addition of Methyl Iodide to [Tp*Rh(CO)(L)]

2002 ◽  
Vol 41 (12) ◽  
pp. 3280-3290 ◽  
Author(s):  
Valérie Chauby ◽  
Jean-Claude Daran ◽  
Carole Serra-Le Berre ◽  
François Malbosc ◽  
Philippe Kalck ◽  
...  
Keyword(s):  
Methyl Iodide ◽  
Oxidative Addition ◽  
Mechanistic Investigation

Evidence of an Oxidative-Addition-Promoted Pd-Leaching Mechanism in the Suzuki Reaction by Using a Pd-Nanostructure Design

2012 ◽  
Vol 18 (32) ◽  
pp. 9813-9817 ◽  
Author(s):  
Zhiqiang Niu ◽  
Qing Peng ◽  
Zhongbin Zhuang ◽  
Wei He ◽  
Yadong Li
Keyword(s):  
Suzuki Reaction ◽  
Oxidative Addition ◽  
Leaching Mechanism
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