Titanium-Catalyzed Reductive Cyclization of .delta.,.epsilon.-Unsaturated Ketones and Aldehydes

Crowe, William E.; Rachita, Michael J.

doi:10.1021/ja00130a022

Cited by 106 publications

(38 citation statements)

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“…Catalytic intramolecular carbonyl vinylation was first reported by Ojima (1994), who employed a rhodium catalyst in combination with a silane as the terminal reductant [159]. Related cyclizations using titanium or nickel catalysts later were reported by Crowe [160] (For an aligned study, see: [161]) and Montgomery [162–167], respectively. Finally, in an adaptation of Montgomery’s cyclization protocol, intermolecular nickel-catalyzed alkyne–aldehyde reductive couplings were reported by Jamison [168–171].…”

Section: Iridium-catalyzed Hydrogenation For C–c Bond Formationmentioning

confidence: 99%

Formation of C–C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation

2010

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The formation of C-C bonds via catalytic hydrogenation and transfer hydrogenation enables carbonyl and imine addition in the absence of stoichiometric organometallic reagents. In this review, iridium-catalyzed C-C bond-forming hydrogenations and transfer hydrogenations are surveyed. These processes encompass selective, atom-economic methods for the vinylation and allylation of carbonyl compounds and imines. Notably, under transfer hydrogenation conditions, alcohol dehydrogenation drives reductive generation of organoiridium nucleophiles, enabling carbonyl addition from the aldehyde or alcohol oxidation level. In the latter case, hydrogen exchange between alcohols and π-unsaturated reactants generates electrophile-nucleophile pairs en route to products of hydro-hydroxyalkylation, representing a direct method for the functionalization of carbinol C-H bonds.

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Section: Iridium-catalyzed Hydrogenation For C–c Bond Formationmentioning

confidence: 99%

Formation of C–C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation

2010

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“…[73][74][75] As previously discussed in the context of early transition metalcatalyzed diene cyclization reactions, stereoselection is often more challenging to control in these cyclization reactions due to competitive kinetic trapping of the intermediate metallacyclopentene before thermodynamic equilibration.…”

Section: Cyclization Reactions Mediated By Metallocenesmentioning

confidence: 99%

5.34 Early Transition Metal Mediated Reductive Coupling Reactions

Micalizio¹

2014

Comprehensive Organic Synthesis II

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“…30,31 The cleavage of the titaniumoxygen bond in the metallacycles 20 by a hydrosilane provides a route to the generation of the active catalyst. The net transformation resembles the above-mentioned complementary radical pathways, which afford the opposite isomer.…”

Section: Scheme 18mentioning

confidence: 99%

A Catalytic System for Reductive Transformations via One-Electron Transfer

Hirao

1999

Synlett

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Recent advances in the catalytic one-electron reduction are the subject of this account. A titanium-, vanadium-or chromium-catalyzed reduction reaction including dehalogenation, pinacol coupling, the McMurry coupling, the related radical cyclization, and the Nozaki-Hiyama-Kishi reaction has been developed by constructing a multi-component system in combination with a co-reductant and additives, which serve for the liberation of the catalyst and the facilitation of the recycling steps. The high stereoselectivity is allowed to be attained in some catalytic reductive bond formations.

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Titanium-Catalyzed Reductive Cyclization of .delta.,.epsilon.-Unsaturated Ketones and Aldehydes

Cited by 106 publications

References 0 publications

Formation of C–C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation

Formation of C–C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation

5.34 Early Transition Metal Mediated Reductive Coupling Reactions

A Catalytic System for Reductive Transformations via One-Electron Transfer

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