Applications of CeCl3 as an Environmental Friendly Promoter in Organic Chemistry

被引：93

作者：

Bartoli, Giuseppe ^{[2
]}

Marcantoni, Enrico ^{[1
]}

Marcolini, Mauro ^{[1
]}

Sambri, Letizia ^{[2
]}

机构：

[1] Univ Camerino, Div Chem, Sch Sci & Technol, I-62032 Camerino, MC, Italy

[2] Univ Bologna, Dept Organ Chem A Mangini, I-40156 Bologna, Italy

来源：

CHEMICAL REVIEWS | 2010年 / 110卷 / 10期

关键词：

CERIUM(III) CHLORIDE HEPTAHYDRATE; BETA-KETOPHOSPHINE OXIDES; BOND-FORMING REACTIONS; MULTICOMPONENT STEREOSELECTIVE-SYNTHESIS; CATALYTIC ASYMMETRIC ALLYLATION; REVERSED STEREOCHEMICAL CONTROL; CARBONYL ADDITION-REACTIONS; ACID MEDIATED REDUCTION; LEWIS BASE ACTIVATION; TRANS DOUBLE-BOND;

D O I：

10.1021/cr100084g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Researchers conducted investigations to demonstrate applications of CeCl3 as an environmental friendly promoter in organic chemistry. It was desirable to use the Grignard reagents as the source of a transferable alkyl group for such reactions, as it was generally the more valuable part of the reagent. The latest information regarding the CeCl3-promoted Grignard addition to hydroxyl ester indicated that the nature of the reactive species was dependent on the manner in which the CeCl3 was activated and on the water content of the system. It was demonstrated that the combination of vinylmagnesium bromide with CeCl3 worked effectively and silylated allyl alcohols were obtained in satisfactory yields. The chemoselective addition of the organometallic species to the ketone functionality promoted by dry CeCl3 also allowed the researchers to develop a new strategy for the synthesis of γ-,γ-dialkyl-α-(alkylmethylene)-γ- butyrolactones.

引用

页码：6104 / 6143

页数：40

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