Dual reactivity of O-alpha-allenyl esters under palladium(0) catalysis: From carbopalladation/allylic alkylation domino sequence to decarboxylative allenylation

作者：Kammerer Pentier Claire^*; Diez Martinez Alba; Oble Julie; Prestat Guillaume; Merino Pedro; Poli Giovanni

来源：Journal of Organometallic Chemistry, 2012, 714: 53-59.

DOI：10.1016/j.jorganchem.2012.03.014

• Palladium
• Allene
• Lactone
• Domino reactions
• Decarboxylative allenylation

In a mechanistically-oriented study, O-alpha-allenyl esters have been evaluated as potential substrates for Pd-catalyzed carbopalladation/allylic alkylation domino sequences and decarboxylative allenylation reactions. The domino sequence turned out to be feasible only with electron-deficient aryl iodides, thereby showing a narrower potential than that previously observed with the malonamide-based series. The decarboxylative allenylation of O-alpha-allenyl esters was also tested and turned out to be practicable with beta-ketoester-based substrates and using specific basic conditions. Plausible reaction mechanisms are proposed to account for the observed reactivities.

• 出版日期2012-9-1