A Metal-Free Reductive N‑Alkylation of Indoles with Aldehydes

A simple metal-free method has been developed for the reductive N-alkylation of indoles employing aldehydes as the alkylating agent and inexpensive Et3SiH as the reductant. A wide range of aromatic and aliphatic aldehydes are viable substrates along with a variety of substituted indoles. In addition...

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Published inOrganic letters Vol. 23; no. 9; pp. 3233 - 3236
Main Authors Clanton, Nicholas A, Spiller, Taylor E, Ortiz, Eliezer, Gao, Zhinong, Rodriguez-Poirier, Juan Manuel, DelMonte, Albert J, Frantz, Doug E
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.05.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALLYLIC ALKYLATION
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Summary:A simple metal-free method has been developed for the reductive N-alkylation of indoles employing aldehydes as the alkylating agent and inexpensive Et3SiH as the reductant. A wide range of aromatic and aliphatic aldehydes are viable substrates along with a variety of substituted indoles. In addition, the method was applied to a one-pot sequential 1,3-alkylation of a substituted indole and successfully demonstrated on a 100 mmol scale.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00179