Engaging Vinylene Carbonate in Ruthenium-Catalyzed Regioselective C-4 Methylenation and C-8 Formylmethylation of Isoquinolinones DOI

Dolly David Thalakottukara,

Thirumanavelan Gandhi

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(75), P. 10358 - 10361

Published: Jan. 1, 2024

Herein, we disclose the first reports on utilization of vinylene carbonate as a C1 methylene source in ruthenium-catalyzed additive controlled regioselective C4-methylenation and weak chelation-assisted C8-formylmethylation isoquinolinones. Adopting both C2 synthon is an important highlight this work. Amide carbonyl acts traceless directing group C8-formylmethylation. Remarkably, reaction, two C-C bonds form one-pot producing dimeric isoquinolinones by employing surrogate presence copper acetate additive. Importantly, unsymmetrical dimers were achievable, albeit low yield. Extensive control experiments are conducted to decipher reaction mechanism. It evident from mechanistic studies, that formation formylmethyl

Language: Английский

Engaging Vinylene Carbonate in Ruthenium-Catalyzed Regioselective C-4 Methylenation and C-8 Formylmethylation of Isoquinolinones DOI

Dolly David Thalakottukara,

Thirumanavelan Gandhi

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(75), P. 10358 - 10361

Published: Jan. 1, 2024

Herein, we disclose the first reports on utilization of vinylene carbonate as a C1 methylene source in ruthenium-catalyzed additive controlled regioselective C4-methylenation and weak chelation-assisted C8-formylmethylation isoquinolinones. Adopting both C2 synthon is an important highlight this work. Amide carbonyl acts traceless directing group C8-formylmethylation. Remarkably, reaction, two C-C bonds form one-pot producing dimeric isoquinolinones by employing surrogate presence copper acetate additive. Importantly, unsymmetrical dimers were achievable, albeit low yield. Extensive control experiments are conducted to decipher reaction mechanism. It evident from mechanistic studies, that formation formylmethyl

Language: Английский

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