Publication

Olefin Cyclopropanations via Sequential Atom Transfer Radical Addition-Dechlorination Reactions

2010
Journal Articles

Abstract

In organic synthesis, cyclopropanation reactions are often performed with Simmons Smith-type reagents or by transition metal catalyzed reactions of olefins with diazo compounds. A novel method for the synthesis of substituted cyclopropanes is described that is based on a two-step reaction sequence. Olefins are reacted with 1,1'-dichlorides in a Ru-catalyzed atom transfer radical addition (ATRA) process and the resulting 1,3-dichlorides are directly converted into cyclopropanes by reductive coupling with magnesium. This one-pot procedure is applicable to a variety of substrates and can be performed in an inter- or intramolecular fashion.

Official source

https://infoscience.epfl.ch/entities/publication/8e994dbf-b921-4dd5-9fd2-06ba7e1034b1

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2010
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/8e994dbf-b921-4dd5-9fd2-06ba7e1034b1

About this result

Related concepts (22)

Cyclopropanation

In organic chemistry, cyclopropanation refers to any chemical process which generates cyclopropane () rings. It is an important process in modern chemistry as many useful compounds bear this motif; for example pyrethroid insecticides and a number of quinolone antibiotics (ciprofloxacin, sparfloxacin, etc.). However, the high ring strain present in cyclopropanes makes them challenging to produce and generally requires the use of highly reactive species, such as carbenes, ylids and carbanions.

Coupling reaction

In organic chemistry, a coupling reaction is a type of reaction in which two reactant molecules are bonded together. Such reactions often require the aid of a metal catalyst. In one important reaction type, a main group organometallic compound of the type R-M (where R = organic group, M = main group centre metal atom) reacts with an organic halide of the type R'-X with formation of a new carbon-carbon bond in the product R-R'. The most common type of coupling reaction is the cross coupling reaction. Richard F.

Cross-coupling reaction

In organic chemistry, a cross-coupling reaction is a reaction where two different fragments are joined. Cross-couplings are a subset of the more general coupling reactions. Often cross-coupling reactions require metal catalysts. One important reaction type is this: (R, R' = organic fragments, usually aryle; M = main group center such as Li or MgX; X = halide) These reactions are used to form carbon–carbon bonds but also carbon-heteroatom bonds. Cross-coupling reaction are a subset of coupling reactions.

Related publications (7)

Olefin Cyclopropanations via Sequential Atom Transfer Radical Addition-Dechlorination Reactions

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