Catalytic Cyclopropanation with Iron(II) Complexes

Hamaker, Christopher G.; Mirafzal, Gholam A.; Woo, L. Keith

doi:10.1021/om010513u

Cited by 104 publications

(58 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[6] Among catalytic systems employed in cyclopropanations, those based on porphyrins surely play a prominent role. [7][8][9][10][11][12][13][14] This microreview is focussed on the catalytic activity of porphyrin complexes of group 9 metals. Recent advances in understanding the mechanism of cyclopropanation mediated by M(porphyrin) complexes (M = Co, Rh) will be highlighted.…”

Section: Introductionmentioning

confidence: 99%

Cyclopropanation Reactions Mediated by Group 9 Metal Porphyrin Complexes

2011

View full text Add to dashboard Cite

Keywords: Cyclopropanation / Diazo compounds / Porphyrins / Cobalt / Rhodium / IridiumThe one-pot reaction of diazo compounds with olefins represents a useful strategy to synthesise cyclopropanes, which are important both as starting materials for the synthesis of organic compounds and because of their intrinsic pharmaceutical properties. Herein we describe the catalytic activity of group 9 metal porphyrin complexes to cyclopropanate ole-

show abstract

Section: Introductionmentioning

confidence: 99%

Cyclopropanation Reactions Mediated by Group 9 Metal Porphyrin Complexes

2011

View full text Add to dashboard Cite

show abstract

“…In 2001, Woo and co-workers [16] reported an efficient Fe(TTP)-catalyzed cyclopropanation of styrene with aryldiazomethanes. Interestingly, a reversal of diastereoselectivity was observed when different diazomethanes were employed (Scheme 3).…”

Section: Methodsmentioning

confidence: 99%

Recent advances in the iron-catalyzed cycloaddition reactions

Wang

Wan

2012

Chin. Sci. Bull.

View full text Add to dashboard Cite

The rapid generation of molecular in a relatively easy manner has made the cycloaddition reaction a powerful tool in the synthesis of different membered ring compounds. Clearly, iron catalysts are becoming a much more interesting and viable choice for this purpose. In this review, a number of promising results in the iron catalyzed cycloaddition reactions in the last decades were summarized. Special attention has been paid to the asymmetric cycloaddition reactions. cycloaddition, iron catalyst, asymmetric Citation:Wang C X, Wan B S. Recent advances in the iron-catalyzed cycloaddition reactions. Chin Sci Bull, 2012, 57: 23382351, doi: 10.1007/s11434-012-5141-z Cycloaddition reaction, which can construct several bonds simultaneously in a single step, is one of the most powerful strategies for the synthesis of cyclic compounds from various unsaturated substrates such as alkynes, alkenes, allenes, nitriles, aldehydes, ketones, imines, etc. Three-, four-, five-, six-or seven-membered rings are obtained through these transformations. The high atom-efficiency, as well as the good tolerance of different functional groups, continues to draw many chemists' attention to this field. In particular, great efforts have been devoted to the development of novel and efficient catalytic systems. However, harsh reaction conditions are often required including heat, light, high pressure or sonication, and the lack of chemo-and/or regioselectivity is also an important problem. Over the past decades, the use of transition metal catalysts has contributed significantly to the development of the cycloaddition reactions and good selectivities were obtained [1]. Among all the available transition metals, iron is generally regarded as one of the most inexpensive, abundant, benign and relatively non-toxic metals [2]. Many transformations have been effectively promoted by iron catalysts, and excellent reviews on the iron-catalyzed reactions are available [3][4][5][6][7][8][9][10][11][12][13][14][15]. Bolm and co-workers [3] summarized the most important transformations with the aid of iron catalysts in 2004, including addition, substitution, cycloaddition, reduction and other reactions. At a later time, they also reviewed the oxidative C-C coupling reactions [4] and the development of carbon-heteroatom and heteroatom-heteroatom bond formation under iron catalysts [5]. The uses of FeCl 3 as catalyst in organic synthesis were covered by Padrón [6] and Bolm [4], and the cross coupling reactions were discussed in detail by Fürstner [7,8]. Recently, direct C-H transformation via iron catalysis was summarized by Shi and co-workers [9]. Applications of iron catalysts on other reactions were also summarized by Bauer [10] However, despite the aforementioned contributions, reviews mainly focus on the iron-catalyzed cycloaddition reactions are rather rare [15]. In this review, we will point out recent advances in this field, most contributions going from 2004 to Nov. 2011. Although every effort has been made to avoid repetition, some overlap with the ...

show abstract

“…[6] Allerdings ist die Carben-Untereinheit von 12 nicht nur an Rhodium sondern auch an ein Corrol-Stickstoffatom gebunden. Aus Metall-Porphyrinen (M = Fe, [7] Ru [8] und Os [9] ) erhielt man jedoch zahlreiche Carben-Komplexe 13, in denen das Carben-Kohlenstoffatom ausschließlich am Metall gebunden ist. Dreizähnige Amin-und Phosphinliganden wurden zur Herstellung der Carben-Komplexe 14 [10] und 15 [11] verwendet.…”

Section: Einführungunclassified

Kupfer‐Carben‐Komplexe: hochentwickelte Katalysatoren, neue Erkenntnisse

Kirmse

2003

Angewandte Chemie

View full text Add to dashboard Cite

Die Steuerung der Selektivität reaktiver Zwischenstufen ist ein wichtiges Ziel in der organischen Chemie. Photochemisch oder thermisch aus Diazoverbindungen erzeugte Carbene lassen sich nicht von außen beeinflussen und bilden Produktgemische. Dagegen führt die katalytische Zersetzung von Diazoverbindungen zu selektiven Carbenoiden, die häufig in der Synthese verwendet werden – bei geringer Kenntnis ihrer Eigenschaften. Andererseits sind zahlreiche Carben‐Metall‐Komplexe bekannt, denen die carbenoide Reaktivität fehlt. Das Zusammenwirken von Experiment und Theorie liefert Informationen über die labilen Zwischenstufen der katalytischen Zersetzung von Diazoverbindungen. Im Mittelpunkt dieses Kurzaufsatzes stehen Kupfer‐Komplexe, doch werden auch andere Metalle berücksichtigt.

show abstract

Catalytic Cyclopropanation with Iron(II) Complexes

Cited by 104 publications

References 50 publications

Cyclopropanation Reactions Mediated by Group 9 Metal Porphyrin Complexes

Cyclopropanation Reactions Mediated by Group 9 Metal Porphyrin Complexes

Recent advances in the iron-catalyzed cycloaddition reactions

Kupfer‐Carben‐Komplexe: hochentwickelte Katalysatoren, neue Erkenntnisse

Contact Info

Product

Resources

About