Reductive Cross‐Coupling between Arylaldehydes and (Hetero)aryl Electrophiles Using Silylboronate Reductant

A catalytic reductive cross‐coupling between arylaldehydes and aryl electrophiles using a silylboronate as a terminal reductant is described. The reaction involves a copper‐catalyzed silylboration of aldehydes affording the O‐borylated α‐silyl alcohols followed by a nucleophilic aromatic substitutio...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-02, Vol.2022 (8), p.n/a
Main Authors: Watanabe, Koh, Takeda, Mitsutaka, Nagao, Kazunori, Ohmiya, Hirohisa
Format: Article
Language:English
Subjects:
Alcohols
Aldehydes
Aromatic compounds
Copper Catalysis
Cross coupling
Reagents
Reducing agents
Reductive Umpolung
Silylboronate
Substitution reactions
Synthetic methods
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Summary:A catalytic reductive cross‐coupling between arylaldehydes and aryl electrophiles using a silylboronate as a terminal reductant is described. The reaction involves a copper‐catalyzed silylboration of aldehydes affording the O‐borylated α‐silyl alcohols followed by a nucleophilic aromatic substitution reaction with aryl electrophiles. This protocol offers a new opportunity to access 1,1‐diarylmethanol derivatives without rare metals or highly basic organometallic reagents. This manuscript describes a catalytic reductive cross‐coupling between arylaldehydes and aryl electrophiles using silylboronate as a terminal reductant. The reaction involves a copper‐catalyzed silylboration of aldehydes affording the O‐borylated α‐silyl alcohols followed by the nucleophilic aromatic substitution reaction with aryl electrophiles. This protocol offers a new opportunity to access 1,1‐diarylmethanol derivatives without rare‐metals and highly basic organometallic reagents.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200005