Rhodium(III)-Catalyzed Direct Coupling of Quinoline-8-Carbaldehydes with (Het)Arylboronic Acids for the Synthesis of 8‑Aryloylquinolines

Herein, we describe a method for the synthesis of aryl-(het)­aryl ketones by Rh­(III)-catalyzed direct coupling between quinoline-8-carbaldehydes and (het)­arylboronic acids. The method has a broad substrate scope, a high functional group tolerance, and uses commercially available starting materials...

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Published inJournal of organic chemistry Vol. 85; no. 15; pp. 10271 - 10282
Main Authors Lyu, Xue-Li, Huang, Shi-Sheng, Huang, Yuan-Qiong, Li, Yong-Qiang, Song, Hong-Jian, Liu, Yu-Xiu, Wang, Qing-Min
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.08.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CARBON BOND FORMATION
BORONIC ACIDS
KETONES
ALDEHYDE
ACYL CHLORIDES
CATALYZED SYNTHESIS
ALKYLATION
ARYLATION
SALICYLALDEHYDES
C-H ACTIVATION
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Summary:Herein, we describe a method for the synthesis of aryl-(het)­aryl ketones by Rh­(III)-catalyzed direct coupling between quinoline-8-carbaldehydes and (het)­arylboronic acids. The method has a broad substrate scope, a high functional group tolerance, and uses commercially available starting materials. Scale-up of the reaction and subsequent synthesis of tubulin polymerization inhibitor demonstrated its utilities. A plausible mechanism was proposed on the basis of the fact that a stable cycloacylrhodium intermediate complex could be used as catalyst, and the complex reacted stoichiometrically with (het)­arylboronic acids.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01490