Lewis Acid Catalyzed Benzylic C-H Bond Functionalization of Azaarenes; Addition to Imines and Enones

被引：31
|
作者：
Komai, Hirotomo [1 ]
Yoshino, Tatsuhiko [1 ]
Matsunaga, Shigeki [1 ,2 ]
Kanai, Motomu [1 ,2 ]
机构：
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
[2] Japan Sci & Technol Agcy, Kanai Life Sci Catalysis Project, ERATO, Bunkyo Ku, Tokyo 1130033, Japan
来源：
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 14期
关键词：
nitrogen heterocycles; C-H bond functionalization; enones; imines; Lewis acids; N-SULFONYL ALDIMINES; SELECTIVE ALKENYLATION; ALKYLATION; ACTIVATION; PYRIDINES; ARYLATION; SP(2); DERIVATIVES; OLEFINATION; HALIDES;
D O I：
10.1055/s-0031-1291041
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Lewis acid catalyzed benzylic C-H bond functionalization of alkyl-substituted azaarenes is described. The addition to N-tosyl imines proceeded under solvent-free conditions using various Lewis acids. Cu(OTf)(2) was the best Lewis acid, and 1,2-addition proceeded at 60-120 degrees C, giving products in 23-92% yield. On the other hand, strongly Lewis acidic rare-earth metal triflates, Sc(OTf)(3) and Y(OTf)(3), were essential to promote the 1,4-addition of alkyl-substituted azaarenes to enones, and products were obtained in 60-96% yield.
引用
收藏
页码：2185 / 2194
页数：10
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