A highly regio- and stereoselective Pd-catalyzed electrocarboxylation of Baylis-Hillman acetates: An interesting switchable regioselectivity based on electrode material

Satyanarayana, T.; Gulipalli, Kali Charan; Endoori, Srinivas; Bodige, Srinu; Pommidi, Anil Kumar; Medaboina, Srinivas; Rejinthala, Swathi; Choppadandi, Suresh; Boya, Ravi; Kanuka, Ashok; Valluri, Muralikrishna

doi:10.1016/j.tetlet.2022.154022

Cited by 5 publications

(1 citation statement)

References 66 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In continuation with our ongoing interest addressing the synthetic valorization of CO 2 8 and the electrochemical manipulation of Morita–Baylis–Hillman (MBH) acetates 1 , 9 we envisioned the possibility of merging these approaches documenting cathodic reduction 10 of MBH derivatives 1 and subsequent CO 2 trapping. 11 Therefore, the electrophilic profile of MBH acetates 1 , previously serving for the capture of nucleophilic radicals 12 generated by cathodic reduction (Scheme 1b ), is manipulated into a nucleophilic character. 13 The interception of the resulting allyl anions A by CO 2 would result in direct access to synthetically valuable succinates 2 (Scheme 1c ).…”

Section: Table 1 Optimization Of the Reaction Conditionsmentioning

confidence: 99%

Catalyst- and Additive-Free Electrochemical CO2 Fixation into Morita–Baylis–Hillman Acetates

2023

View full text Add to dashboard Cite

The electrochemical carboxylation of Morita-Baylis-Hillman (MBH) acetates with CO2 is presented. The process proceeds in the absence of transition metal catalysts and relies on the cathodic reduction of MBH acetates to generate nucleophilic anions able to trap low-pressure CO2. Valuable succinate derivatives are obtained (20 examples) in high yields (up to 90%) and high functional group tolerance. A remarkable substrate controlled (electronic nature) regioselectivity of the transformation was documented along with a mechanistic rationale based on control experiments.

show abstract

Section: Table 1 Optimization Of the Reaction Conditionsmentioning

confidence: 99%