Ruthenium(II)-Catalyzed Grignard-Type Nucleophilic Addition of C(sp2)–H Bonds to Unactivated Aldehydes

The Grignard-type nucleophilic addition of C­(sp2)–H bonds to aldehydes catalyzed by high-oxidation-state transition metal complexes is limited to activated aldehydes. Herein, we report the first example of Grignard-type nucleophilic addition of C­(sp2)–H bonds to unactivated aldehydes catalyzed by...

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Published inJournal of organic chemistry Vol. 87; no. 21; pp. 14723 - 14730
Main Authors Yang, Lidong, Liu, Zezhao, Tang, Tingyu, Tang, Shibiao, Li, Bin, Wang, Baiquan
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.11.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
ACTIVATION
COUPLING REACTIONS
ARYLATION
INDOLINES
CATALYZED DIRECT ADDITION
CLEAVAGE
C-H BONDS
DIRECT HYDROXYMETHYLATION
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Summary:The Grignard-type nucleophilic addition of C­(sp2)–H bonds to aldehydes catalyzed by high-oxidation-state transition metal complexes is limited to activated aldehydes. Herein, we report the first example of Grignard-type nucleophilic addition of C­(sp2)–H bonds to unactivated aldehydes catalyzed by high-oxidation-state ruthenium­(II). The reaction has mild reaction conditions and good functional group tolerance. The corresponding alcohol products are obtained in good to excellent yields.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02039