Rh( i )-catalyzed site-selective hydroacylation of alkenyl-bearing allylic alcohols with non-chelating aldehydes controlled by in situ generated carbonyl group

A rhodium( i )-catalyzed regioselective hydroacylation of alkenyl-bearing allylic alcohols with simple aldehydes for the preparation of diverse 1,5-diketones is described. Mechanistic investigation suggests that this transformation might proceed through redox isomerization of the allylic alcohol fol...

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Bibliographic Details
Published in:New journal of chemistry 2022-10, Vol.46 (41), p.19802-19807
Main Authors: Wang, Fu-Gang, Gong, Fei-Yuan, Cao, Juan, Wang, Ji-Cong, Tian, Kai-Qiang, Zhao, Jinbo, Li, Hong-Shuang
Format: Article
Language:English
Subjects:
Alcohols
Aldehydes
Carbonyl groups
Carbonyls
Chelation
Diketones
Isomerization
Rhodium
Selectivity
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Summary:A rhodium( i )-catalyzed regioselective hydroacylation of alkenyl-bearing allylic alcohols with simple aldehydes for the preparation of diverse 1,5-diketones is described. Mechanistic investigation suggests that this transformation might proceed through redox isomerization of the allylic alcohol followed by hydroacylation of the resulting enone with aldehyde involving a stable six-membered rhodacycle intermediate. This protocol highlights the role of in situ generated carbonyl group in controlling the site-selectivity of the intramolecular alkene moiety.
ISSN:1144-0546
1369-9261
DOI:10.1039/D2NJ04607E