Synthesis of ferrocenes with ene-terminus via water-promoted Barbier-like carbonyl allylation using bimetallic copper(II)/tin(II) reagent

被引：10

作者：

Debroy, P ^{[1
]}

Roy, S ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Organomet & Catalysis Lab, Kharagpur 721302, W Bengal, India

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2003年 / 675卷 / 1-2期

关键词：

alkenylferrocene; 1,3-butadienylferrocene; 3]-oxa-ferrocenophane; allyltin; allylation;

D O I：

10.1016/S0022-328X(03)00205-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 [无机化学]; 081704 [应用化学];

摘要：

Barbier-type gamma-regiospecific allylation of formylferrocene (1) with allyl bromides in the presence of stannous chloride dihydrate and catalytic cupric chloride in dichloromethane-water (1:1) afforded corresponding ferrocenyl dienes FcCHC(R-1)C(R-2)CH2 (36). On the other hand, similar reactions of 1,1'-bis-formylferrocene (2) yielded oxa-bridged [3]-ferrocenophanes having allyl pendants Fc[CH2C(R-2)CH(R-1)CH-mu(O)-CHCH(R-1)C(R-2)CH2] (8-11). The latter appear to result from the dehydration of intermediate homoallylic alcohols. Dehydration could be arrested in case of reaction of I and 2 with 1-bromo-3-methyl-but-2-ene, which results in the formation of homoallylic alcohols FcCH(OH)C(Me-2)CHCH2 (7) and Fc[CH(OH)C(Me-2)CHCH2](2) (12), respectively. All the reactions completely fail in absence of water. (C) 2003 Elsevier Science B.V. All rights reserved.

引用

页码：105 / 112

页数：8

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