Palladium-Catalyzed Formal (5+2) Annulation between ortho-Alkenylanilides and Allenes

被引：52

作者：

Cendon, Borja ^{[1
,2
]}

Casanova, Noelia ^{[1
,2
]}

Comanescu, Cezar ^{[1
,2
,4
]}

Garcia-Fandino, Rebeca ^{[1
,2
,3
]}

Seoane, Andres ^{[1
,2
]}

Gulias, Moises ^{[1
,2
]}

Mascarenas, Jose L. ^{[1
,2
]}

机构：

[1] Univ Santiago de Compostela, Ctr Singular Invest Quim Biol & Mat Mol CIQUS, Santiago De Compostela 15782, Spain

[2] Univ Santiago de Compostela, Dept Quim Organ, Santiago De Compostela 15782, Spain

[3] Univ Porto, Fac Sci, Dept Chem & Biochem, CIQUP, R Campo Alegre S-N, P-4169007 Oporto, Portugal

[4] Univ Politehn Bucuresti, Dept Inorgan Chem, 1 Polizu St, RO-011061 Bucharest, Romania

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 07期

基金：

欧洲研究理事会;

关键词：

C-H FUNCTIONALIZATION; INTERMOLECULAR CYCLOADDITIONS; ACTIVATION; ALKYNES; CYCLIZATION; AMINATION; 2-ALKENYLPHENOLS; HETEROCYCLES; TEMPERATURE; CARBAZOLES;

D O I：

10.1021/acs.orglett.7b00467

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Alkenyltriflylanilides react with allenes upon treatment with catalytic amounts of Pd(OAc)(2) and Cu(II) to give highly valuable: 2,3-dihydro-1H-benzo[b]azepines, in good yields, and with very high regio- and diastereoselectivities. Density functional theory (DFT) calculations suggest that the C-H activation of the alkenylanilide involves a classical concerted metalation-deprotonation (CMD) mechanism.

引用

页码：1674 / 1677

页数：4

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