Article: Decarboxylative Allylic Alkylation of Phthalides: Stabilized Benzylic Nucleophiles for sp³–sp³ Coupling
Journal of organic chemistry. 2022 May 16, v. 87, no. 11
2022
Abstract: A new family of stabilized benzylic nucleophiles for the palladium-catalyzed decarboxylative allylic alkylation reaction has been developed. Allyl esters derived from 3-carboxyphthalides were found to undergo palladium-catalyzed deallylation and ... ...
Abstract | A new family of stabilized benzylic nucleophiles for the palladium-catalyzed decarboxylative allylic alkylation reaction has been developed. Allyl esters derived from 3-carboxyphthalides were found to undergo palladium-catalyzed deallylation and decarboxylation under mild reaction conditions, a process facilitated by the formation of a stabilized aromatic anion. The regioselective allylic coupling of this intermediate afforded a variety of functionalized phthalides in 73–96% yields. |
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Keywords | Lewis bases ; alkylation ; decarboxylation ; new family ; organic chemistry ; phthalides ; regioselectivity |
Language | English |
Dates of publication | 2022-0516 |
Size | p. 7557-7564. |
Publishing place | American Chemical Society |
Document type | Article |
ZDB-ID | 123490-0 |
ISSN | 1520-6904 ; 0022-3263 |
ISSN (online) | 1520-6904 |
ISSN | 0022-3263 |
DOI | 10.1021/acs.joc.2c00723 |
Database | NAL-Catalogue (AGRICOLA) |
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