Accessing α-Arylated Nitriles via BF3•OEt2 Catalyzed Cyanation of para-Quinone Methides Using tert-Butyl Isocyanide as a Cyanide Source

被引：45

作者：

Shirsath, Sachin R. ^{[1
,2
]}

Shinde, Ganesh H. ^{[1
]}

Shaikh, Aslam C. ^{[1
]}

Muthukrishnan, M. ^{[1
,2
]}

机构：

[1] CSIR Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India

[2] Acad Sci & Innovat Res AcSIR, New Delhi 110025, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 19期

关键词：

1,6-CONJUGATE ADDITION; ASYMMETRIC-SYNTHESIS; EXPEDIENT ACCESS; BOND FORMATION; ALDOXIMES; ACID; CYCLOADDITION; HYDROXYLATION; DEHYDRATION; OLEFINATION;

D O I：

10.1021/acs.joc.8b01926

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：12305 / 12314

页数：10