Accessing alpha-arylated nitriles via BF3 center dot OEt2 catalyzed cyanation of para-quinone methides using tert-butyl isocyanide as a cyanide source

Title Accessing alpha-arylated nitriles via BF3 center dot OEt2 catalyzed cyanation of para-quinone methides using tert-butyl isocyanide as a cyanide source
Publication TypeJournal Article
Year of Publication2018
AuthorsShirsath, SR, Shinde, GH, Shaikh, AC, Muthukrishnan, M
JournalJournal of Organic Chemistry
Volume83
Issue19
Pagination12305-12314
Date PublishedOCT
Type of ArticleArticle
ISSN 0022-3263
Abstract

BF3 center dot OEt2 catalyzed 1,6-conjugate addition of tertbutyl isocyanide to para-quinone methides and fuchsones for the synthesis of alpha-diaryl and alpha-triaryl nitriles has been reported. This protocol allows alpha-diaryl- and alpha-triaryl nitriles to be accessed in good to excellent yields and with a broad substrate scope, which could be further functionalized to give a versatile set of products. This is the first example wherein tert-butyl isocyanide has been used as a cyanide source for the 1,6-conjugate addition.

DOI10.1021/acs.joc.8b01926
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

4.805

Divison category: 
Organic Chemistry