Accessing 4-oxy-substituted isoquinolinones via C–H activation and regioselective migratory insertion with electronically biased ynol ethers

2018 ◽  
Vol 16 (44) ◽  
pp. 8639-8646 ◽  
Author(s):  
Brandon L. Coles-Taylor ◽  
Maximilian S. McCallum ◽  
J. Scott Lee ◽  
Brian W. Michel
Keyword(s):  
Migratory Insertion ◽  
Ynol Ethers

The rhodium-catalyzed C–H activation and annulation with ynol ethers to directly provide 4-oxy substituted isoquinolinones is reported.

Access to Substituted Indenol Ethers via a Regioselective Intermolecular Carbopalladation Cascade

2019 ◽  
Author(s):  
Brandon L. Coles-Taylor ◽  
Maximilian S. McCallum ◽  
Andrés G. Muñoz ◽  
Brian Michel
Keyword(s):  
Heck Reaction ◽  
Reductive Elimination ◽  
Catalytic Cycle ◽  
Reaction Conditions ◽  
Powerful Approach ◽  
Migratory Insertion ◽  
Ynol Ethers ◽  
Hydride Elimination ◽  
Turn Over

Alkyne carbopalladation reactions represent a powerful approach to generating multiple new C–C bonds and substituted alkenes, however regioselectivity is often challenging for intermolecular variants. By utilizing ynol ethers as polarized alkynes we observe complete regiocontrol of migratory insertion with Pd–Ar species. A Heck reaction was used to turn-over the catalytic cycle by intercepting the vinyl-Pd adduct of carbopalladation with a pendant alkene. When using <i>o</i>-iodo styrenes substrates the resulting products are oligosubstituted 1-indenol ethers with defined stereochemistry based on the initial alkene geometry. By blocking β-hydride elimination we demonstrated C–H and C–C reductive elimination steps for catalyst turnover. Herein we report the optimization of reaction conditions, scope, and alternative termination steps.

Access to Substituted Indenol Ethers via a Regioselective Intermolecular Carbopalladation Cascade

2019 ◽  
Author(s):  
Brandon L. Coles-Taylor ◽  
Maximilian S. McCallum ◽  
Andrés G. Muñoz ◽  
Brian Michel
Keyword(s):  
Heck Reaction ◽  
Reductive Elimination ◽  
Catalytic Cycle ◽  
Reaction Conditions ◽  
Powerful Approach ◽  
Migratory Insertion ◽  
Ynol Ethers ◽  
Hydride Elimination ◽  
Turn Over

Alkyne carbopalladation reactions represent a powerful approach to generating multiple new C–C bonds and substituted alkenes, however regioselectivity is often challenging for intermolecular variants. By utilizing ynol ethers as polarized alkynes we observe complete regiocontrol of migratory insertion with Pd–Ar species. A Heck reaction was used to turn-over the catalytic cycle by intercepting the vinyl-Pd adduct of carbopalladation with a pendant alkene. When using <i>o</i>-iodo styrenes substrates the resulting products are oligosubstituted 1-indenol ethers with defined stereochemistry based on the initial alkene geometry. By blocking β-hydride elimination we demonstrated C–H and C–C reductive elimination steps for catalyst turnover. Herein we report the optimization of reaction conditions, scope, and alternative termination steps.

NO Migratory Insertion into Ruthenium–Aryl Bond with a Hydridotris(pyrazolyl)borato Ligand

2021 ◽  
Vol 40 (3) ◽  
pp. 302-305
Author(s):  
Yasuhiro Arikawa ◽  
Motoki Yamada ◽  
Nobuko Takemoto ◽  
Shinnosuke Horiuchi ◽  
Eri Sakuda ◽  
...  
Keyword(s):  
Migratory Insertion

CO and Ethylene Migratory Insertion Reactions and Copolymerization Involving Palladium Complexes of a NiN2S2Metallodithiolate Ligand

2007 ◽  
Vol 26 (4) ◽  
pp. 783-792 ◽  
Author(s):  
Marilyn V. Rampersad ◽  
Erik Zuidema ◽  
Jan Meine Ernsting ◽  
Piet W. N. M. van Leeuwen ◽  
Marcetta Y. Darensbourg
Keyword(s):  
Palladium Complexes ◽  
Insertion Reactions ◽  
Migratory Insertion
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