Reductive Cross‐Coupling between Arylaldehydes and (Hetero)aryl Electrophiles Using Silylboronate Reductant. Issue 8 (21st February 2022)

• Record Type: Journal Article
• Authors: Watanabe, Koh; Takeda, Mitsutaka; Nagao, Kazunori; Ohmiya, Hirohisa
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 8(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-02-21
• Subjects: Copper Catalysis -- Cross-Coupling -- Reductive Umpolung -- Silylboronate -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200005
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : 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.