Merging Iridium-Catalyzed C–H Borylations with Palladium-Catalyzed Cross-Couplings Using Triorganoindium Reagents

A versatile and efficient method to prepare borylated arenes furnished with alkyl, alkenyl, alkynyl, aryl, and heteroaryl functional groups is developed by merging Ir-catalyzed C–H borylations (CHB) with a chemoselective palladium-catalyzed cross-coupling of triorganoindium reagents (Sarandeses–Sest...

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Published inJournal of organic chemistry Vol. 87; no. 1; pp. 751 - 759
Main Authors Jayasundara, Chathurika R. K, Gil-Negrete, José M, Montero Bastidas, Jose R, Chhabra, Arzoo, Martínez, M. Montserrat, Pérez Sestelo, José, Smith, Milton R, Maleczka, Robert E
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.01.2022
Amer Chemical Soc
Subjects
Boron
Catalysis
Chemistry
Chemistry, Organic
Indicators and Reagents
Iridium
Palladium
Physical Sciences
Science & Technology
ARYL BROMIDES
ACTIVATION
IPSO-BORYLATION
BUILDING-BLOCKS
BORONATE ESTERS
CONSTRUCTION
ARENES
BONDS
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Summary:A versatile and efficient method to prepare borylated arenes furnished with alkyl, alkenyl, alkynyl, aryl, and heteroaryl functional groups is developed by merging Ir-catalyzed C–H borylations (CHB) with a chemoselective palladium-catalyzed cross-coupling of triorganoindium reagents (Sarandeses–Sestelo coupling) with aryl halides bearing a boronic ester substituent. Using triorganoindium cross-coupling reactions to introduce unsaturated moieties enables the synthesis of borylated arenes that would be difficult to access through the direct application of the CHB methodology. The sequential double catalyzed procedure can be also performed in one vessel.
Bibliography:National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01978