Iodide as a Nucleophilic Trigger in Aryne Three-Component Coupling for the Synthesis of 2-lodobenzyl Alcohols

The synthetic potential of KI as the iodide source in aryne three-component coupling has been demonstrated using aldehydes as the third component. This mild and transition-metal free coupling reaction allowed the straightforward synthesis of 2-iodobenzyl alcohols in moderate to good yields with good...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 11; pp. 4383 - 4387
Main Authors Bhattacharjee, Subrata, Guin, Avishek, Gaykar, Rahul N., Biju, Akkattu T.
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 07.06.2019
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
INSERTION
AMINOSILANES
EMPLOYING ARYNES
N-HETEROAROMATICS
TERMINAL ALKYNES
BOND
TRANSITION-METAL-FREE
STRAIGHTFORWARD SYNTHESIS
ACCESS
MULTICOMPONENT REACTION
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Summary:The synthetic potential of KI as the iodide source in aryne three-component coupling has been demonstrated using aldehydes as the third component. This mild and transition-metal free coupling reaction allowed the straightforward synthesis of 2-iodobenzyl alcohols in moderate to good yields with good functional group compatibility. Moreover, KBr and KCl could be used as the nucleophilic trigger in this aryne multicomponent coupling (MCC) and N-methylisatin and CO2 could be used as the electrophilic third components.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01621