4-Aryl- and 4-vinyl-2,2-dialkyl-3-chromenes from tertiary 3-(o-bromophenyl)propynols via a palladium-catalyzed hydroarylation/hydrovinylation-cyclization sequence

被引：17
作者：
Arcadi, A
Cacchi, S
Fabrizi, G
Marinelli, F
Verdecchia, M
机构：
[1] Univ Roma La Sapienza, Dipartimento Studi Chim & Tecnol Sostanze Biol At, I-00185 Rome, Italy
[2] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67100 Laquila, Italy
来源：
SYNLETT | 2006年 / 06期
关键词：
chromenes; palladium catalysis; cyclization; hydrovinylation; hydroarylation;
D O I：
10.1055/s-2006-939048
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
4-Aryl- and 4-vinyl-2,2-dialkyl-3-chromenes were prepared from tertiary 3-(o-bromoplienyl)propynols and aryl iodides or vinyl triflates through a one-pot process, which involves the addition of t-BuONa, dppf and, where appropriate, fresh Pd(OAc)(2) to the crude Mixture resulting from the hydroarylation or hydrovinylation step [Pd(OAc)(2), Et3N, HCOOH, BU4NCI, toluene]. In general, 4-aryl- and 4-vinyl-2,2-dialkyl-3-chromenes are obtained with high regioselectivity and overall yields range from satisfactory to high. Vinyl triflates tend to give higher yields than aryl iodides.
引用
收藏
页码：909 / 915
页数：7
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