N-Heterocyclic Carbene Catalyzed 1,6-Conjugate Addition of Me3Si-CN to para-Quinone Methides and Fuchsones: Access to α-Arylated Nitriles

被引：87
作者：
Goswami, Prithwish [1 ]
Singh, Gurdeep [1 ]
Anand, Ramasamy Vijaya [1 ]
机构：
[1] Indian Inst Sci Educ & Res IISER, Dept Chem Sci, Sect 81, Manauli PO, Sas Nagar 140306, Punjab, India
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 08期
关键词：
AROMATIC-ALDEHYDES; IMIDAZOLIUM CARBOXYLATES; CONJUGATE ADDITION; EXPEDIENT ACCESS; ALKYL CHLORIDES; BOND FORMATION; EFFICIENT; CARBON; ACTIVATION; ALDOXIMES;
D O I：
10.1021/acs.orglett.7b00508
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An organocatalytic approach toward a-arylated nitriles using N-heterocyclic carbene (NHC) as a catalyst is described. This protocol comprises an NHC catalyzed activation of Me3Si-CN followed by 1,6-conjugate addition of cyanide to para-quinone methides (p-QMs) and fuchsones leading to alpha-diaryl- and a-triaryl nitriles in good to excellent yields.
引用
收藏
页码：1982 / 1985
页数：4
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共 88 条
[81]   A general method for the direct α-arylation of nitriles with aryl chlorides [J].
You, JS ;
Verkade, JG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (41) :5051-5053
[82]   Organoselenium-Catalyzed Mild Dehydration of Aldoximes: An Unexpected Practical Method for Organonitrile Synthesis [J].
Yu, Lei ;
Li, Hongyan ;
Zhang, Xu ;
Ye, Jianqing ;
Liu, Jianping ;
Xu, Qing ;
Lautens, Mark .
ORGANIC LETTERS, 2014, 16 (05) :1346-1349
[83]   Bifunctional Organo/Metal Cooperatively Catalyzed [3+2] Annulation of para-Quinone Methides with Vinylcyclopropanes: Approach to Spiro[4.5]deca-6,9-diene-8-ones [J].
Yuan, Zhenbo ;
Wei, Weiwei ;
Lin, Aijun ;
Yao, Hequan .
ORGANIC LETTERS, 2016, 18 (14) :3370-3373
[84]   Dehydration of Aldoximes Using PhSe(O)OH as the Pre-Catalyst in Air [J].
Zhang, Xu ;
Sun, Jingjing ;
Ding, Yuanhua ;
Yu, Lei .
ORGANIC LETTERS, 2015, 17 (23) :5840-5842
[85]   Bismuth-catalyzed allylation of para-quinone methides [J].
Zhang, Zhi-Pei ;
Dong, Nan ;
Li, Xin .
CHEMICAL COMMUNICATIONS, 2017, 53 (07) :1301-1304
[86]   Asymmetric Organocatalytic Synthesis of 3-Diarylmethine-Substituted Oxindoles Bearing a Quaternary Stereocenter via 1,6-Conjugate Addition to para-Quinone Methides [J].
Zhao, Kun ;
Zhi, Ying ;
Wang, Ai ;
Enders, Dieter .
ACS CATALYSIS, 2016, 6 (02) :657-660
[87]   A General and Convenient Catalytic Synthesis of Nitriles from Amides and Silanes [J].
Zhou, Shaolin ;
Junge, Kathrin ;
Addis, Daniele ;
Das, Shoubhik ;
Beller, Matthias .
ORGANIC LETTERS, 2009, 11 (11) :2461-2464
[88]   Chemistry of puupehenone: 1,6-conjugate addition to its quinone-methide system [J].
Zjawiony, JK ;
Bartyzel, P ;
Hamann, MT .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (12) :1502-1508
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