Mischmetall:  An Efficient and Low Cost Coreductant for Catalytic Reactions of Samarium Diiodide

Hélion, Florence; Namy, Jean‐Louis

doi:10.1021/jo9820667

Cited by 63 publications

(33 citation statements)

References 13 publications

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“…Using an inexpensive alloy of the light lanthanides, acetophenone can be reductively coupled in 70 % yield without Me 3 SiCl. [70] However, no reaction takes place in the absence of SmI 2 .…”

Section: Pinacol Couplingmentioning

confidence: 99%

“Asymmetric” Catalysis by Lanthanide Complexes

Mikami

Terada

Matsuzawa

2002

Angew. Chem. Int. Ed.

232

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velopment of asymmetric Ln catalysts, and their recyclable use, is of increasing importance. This review gives an overview of the most recent developments in catalysis with lanthanide(ii) and lanthanide(iii) complexes. REVIEWS[ + ] The elements specified in Figure 1 include scandium and yttrium, which are not formally defined as lanthanide elements, but as rare earth metals. For the sake of simplicity, in this review these two elements are also abbreviated to Ln.

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Section: Pinacol Couplingmentioning

confidence: 99%

“Asymmetric” Catalysis by Lanthanide Complexes

Mikami

Terada

Matsuzawa

2002

Angew. Chem. Int. Ed.

232

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“…Several conditions, such as using a radical mediator (e.g. tin hydride 47 and samarium diiodide 8 ) or light irradiation, 9 have been reported. Meanwhile, we have studied electro-organic transformations, 1013 and recently reported electro-reductive intramolecular cyclization of haloarenes bearing an alkene moiety in acetonitrile.…”

Section: Introductionmentioning

confidence: 99%

Electro-reductive Halogen-Deuterium Exchange and Methylation of Aryl Halides in Acetonitrile

et al. 2013

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“…[11,12] For example, Barbier-type reactions have been studied [13] (Scheme 3). [ Mischmetall, an alloy of the light lanthanides (Ce, La, Nd and Pr), also known as cerium mixed metal, is obtained from bastnaesite (a lanthanide ore).…”

Section: Introductionmentioning

confidence: 99%

Reductive Coupling of Allylic Esters with Carbonyl Compounds Mediated by the Mischmetall/[SmI₂/Pd⁰_cat.′]_cat. System

2005

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The mischmetall/[SmI2/Pd0cat.′]cat. system has been used to mediate the allylation of ketones using a variety of allylic esters (acetates, carbonates and phosphates). Thus, a “two‐stage catalysis” has been carried out using SmI2 and Pd(PPh3)4 in catalytic amounts together with mischmetall (an alloy of the light lanthanides) as a co‐reductant. A catalytic scheme that takes into account previously reported reactions of SmI2/Pd0cat. and mischmetall/SmI2,cat. systems is proposed. It has also been shown that palladium complexes catalyse the addition of organolanthanide species to ketones. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Mischmetall: An Efficient and Low Cost Coreductant for Catalytic Reactions of Samarium Diiodide

Cited by 63 publications

References 13 publications

“Asymmetric” Catalysis by Lanthanide Complexes

“Asymmetric” Catalysis by Lanthanide Complexes

Electro-reductive Halogen-Deuterium Exchange and Methylation of Aryl Halides in Acetonitrile

Reductive Coupling of Allylic Esters with Carbonyl Compounds Mediated by the Mischmetall/[SmI₂/Pd⁰_cat.′]_cat. System

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Mischmetall: An Efficient and Low Cost Coreductant for Catalytic Reactions of Samarium Diiodide

Cited by 63 publications

References 13 publications

“Asymmetric” Catalysis by Lanthanide Complexes

“Asymmetric” Catalysis by Lanthanide Complexes

Electro-reductive Halogen-Deuterium Exchange and Methylation of Aryl Halides in Acetonitrile

Reductive Coupling of Allylic Esters with Carbonyl Compounds Mediated by the Mischmetall/[SmI2/Pd0cat.′]cat. System

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Reductive Coupling of Allylic Esters with Carbonyl Compounds Mediated by the Mischmetall/[SmI₂/Pd⁰_cat.′]_cat. System