Palladium-Catalyzed Ring Opening of Cyclobutanones with Carbon- and Heteroatom-Centered Nucleophiles

The transformation of cyclobutanones into acyclic carbonyl compounds through a Pd-catalyzed C-C bond cleavage is reported. The use of an N-heterocyclic carbene ligand efficiently promoted the ring opening and functionalization of various cyclobutanones, not only with alcohols, but also with N-center...

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Bibliographic Details
Published inSynlett Vol. 34; no. 20; pp. 2486 - 2490
Main Authors Ano, Yusuke, Takahashi, Daichi, Yo, Kazumune, Nagamune, Ryosuke, Chatani, Naoto
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 29.04.2023
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
palladium catalysis
arylboronate esters
C BOND-CLEAVAGE
ACTIVATION
ring opening
C-C bond activation
ACIDS
ESTERS
cyclobutanones
N-heterocyclic carbenes
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Summary:The transformation of cyclobutanones into acyclic carbonyl compounds through a Pd-catalyzed C-C bond cleavage is reported. The use of an N-heterocyclic carbene ligand efficiently promoted the ring opening and functionalization of various cyclobutanones, not only with alcohols, but also with N-centered nucleophiles, such as aniline or amide derivatives. Cyclobutanones were also found to react with arylboronic esters, resulting in the production of acyclic aryl ketones.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0042-1751474