Coupling of Allylic Halides by Nickel Carbonyl

Webb, Irving D.; Borcherdt, G. T.

doi:10.1021/ja01150a068

Cited by 40 publications

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Section: S (23mentioning

confidence: 97%

“…Related to these results is the interesting trimerization of (35) to give (36), Scheme 25.8 In an elegant study, Corey ef al. showed that (39, (37), and (38) +(35) all give (36) on treatment with Ni(CO),.' This behaviour is very interesting as (38) preferentially undergoes intermolecular reaction with (35) followed by ring closure to the 9-membered ring, rather than intramolecular reaction to give the 6- interference of the allylic acetate function.…”

Section: S (23mentioning

confidence: 97%

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π-Allylnickel halides as selective reagents in organic synthesis

Billington¹

1985

Chem. Soc. Rev.

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n-Allylnickel Halides as Selective Reagents in Organic SynthesisThe present review is concerned with the selectivity that is available by the use of n-allylnickel halides for the formation of new carbon-carbon bonds. A general outline of the preparation of the complexes, their structure and physical properties is followed by an analysis of their reactivity patterns. Examples of the use of the complexes in natural-product syntheses are then presented, grouped by 'electrophile'.It is hoped that this treatment will demonstrate the utility of these complexes to organic chemists and stimulate their wider use as reagents. Preparation, Structure, and PropertiesThe dimeric n-allylnickel halide complexes are most conveniently prepared by the reaction of allylic halides with a zero-valent nickel species, in a non-polar solvent, Scheme 3. The two most commonly used nickel species are nickeltetracarbonyl [Ni(C0),l6 and bis-1,5-cyclo-octadienylnickel(0) [Ni(COD)2].7 The use of other nickel species e.g. Ni(C0)3P(Ph)3 has been reported.* Ni(C0)4 is commercially available, and although Ni(COD)2 is also an article of commerce, its high price makes its synthesis attractive. Scbeme 3Allylic systems with other leaving groups such as me~ylates,~ acetates,'O and sulphonium salts l 1 also give rise to n-allylnickel halides on treatment with nickel(0) reagents. The use of allylic bromides is, however, by far the most common procedure, as these compounds are easily and reliably prepared from the corresponding alcohols, and give somewhat higher yields of the complexes.

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Section: S (23mentioning

confidence: 97%

Section: S (23mentioning

confidence: 97%

π-Allylnickel halides as selective reagents in organic synthesis

Billington¹

1985

Chem. Soc. Rev.

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“…In this way, it is easy to obtain $-methyl-branched terminally unsaturated olefins with the most diverse chain lengths. The reaction of methallyl chloride with sodium amide in liquid ammonia also gives 2,5-dimethylhexadiene [33].…”

Section: The Manufacture Of Isobutene Glycol (2-methylpropane-l2-diol)mentioning

confidence: 99%

The Chlorination of the Olefins

Asinger¹

1968

Mono-Olefins

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“…Detailed descriptions of TM-catalyzed allylic transformations have been well-documented and therefore readers are referred to some excellent reviews published elsewhere. [4] Although allylic substitution reactions mediated by Ni date back to 1943, [5] the first catalytic conversion was reported by Felkin and coworkers in 1968 using catalytic amounts of Ni(PPh 3 ) 2 Cl 2 in the reaction between allylic alcohol and alkyl Grignard reagents. [6] Since then, this branch within the area of allylic substitution chemistry with a specific focus on Ni-catalysis has flourished exponentially.…”

Section: Introductionmentioning

confidence: 99%

Nickel‐Catalyzed Allylic Substitution Reactions: An Evolving Alternative

2021

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Transition metal-catalyzed allylic substitution reactions represent versatile transformations in organic synthesis forging CÀ C and C-heteroatom bonds. Despite major contributions realized with precious transition metals, earth-abundant nickel catalysis over the years has emerged as a relative sustainable and efficient alternative in the area of allylic substitution reactions. During the last two decades, the field has witnessed successful accomplishments of chemo-, regio-and enantioselective conversions affording a plethora of products through the employment of Ni-based methodologies. In this Minireview, the most imperative contributions will be discussed with special attention for the more sustainable character and unique reactivity of Ni, the overall process selectivity features and the functional group tolerance and product scope.

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Coupling of Allylic Halides by Nickel Carbonyl

Cited by 40 publications

References 0 publications

π-Allylnickel halides as selective reagents in organic synthesis

π-Allylnickel halides as selective reagents in organic synthesis

The Chlorination of the Olefins

Nickel‐Catalyzed Allylic Substitution Reactions: An Evolving Alternative

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