Phosphinous Acid Platinum Complex as Robust Catalyst for Oxidation: Comparison with Palladium and Mechanistic Investigations

Romain Membrat; Alexandre Vasseur; Alexandre Martinez; Laurent Giordano; Didier Nuel

doi:10.1002/ejoc.201801040

Phosphinous Acid Platinum Complex as Robust Catalyst for Oxidation: Comparison with Palladium and Mechanistic Investigations

European Journal of Organic Chemistry ◽

10.1002/ejoc.201801040 ◽

2018 ◽

Vol 2018 (39) ◽

pp. 5427-5434 ◽

Cited By ~ 3

Author(s):

Romain Membrat ◽

Alexandre Vasseur ◽

Alexandre Martinez ◽

Laurent Giordano ◽

Didier Nuel

Keyword(s):

Platinum Complex ◽

Phosphinous Acid ◽

Mechanistic Investigations

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[RuCl2(η6-p-cymene)] complexes bearing phosphinous acid ligands: preparation, application in C–H bond functionalization and mechanistic investigations

Dalton Transactions ◽

10.1039/c5dt04683a ◽

2016 ◽

Vol 45 (15) ◽

pp. 6491-6502 ◽

Cited By ~ 18

Author(s):

Lionel V. Graux ◽

Michel Giorgi ◽

Gérard Buono ◽

Hervé Clavier

Keyword(s):

Secondary Phosphine ◽

Phosphine Oxides ◽

Phosphinous Acid ◽

Bond Functionalization ◽

Mechanistic Investigations

A series of [RuCl2(η6-p-cymene)] complexes bearing phosphinous acid (PA) ligands have been straightforwardly prepared from the dimer [RuCl2(p-cymene)]2 and secondary phosphine oxides (SPOs) and fully characterized.

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Three-Component [1+1+1] Cyclopropanation with Ruthenium(II)

10.26434/chemrxiv.6025772 ◽

2018 ◽

Author(s):

Tanner C. Jankins ◽

Robert R. Fayzullin ◽

Eugene Khaskin

Keyword(s):

Quaternary Carbon ◽

Poor Control ◽

One Step ◽

Synthetic Routes ◽

Mechanistic Investigations ◽

Chiral Centers ◽

Metal Catalyzed ◽

The Right ◽

Substituted Cyclopropanes

We report a one-step, Ru(II)-catalyzed cyclopropanation reaction that is conceptually different from the previously reported protocols that include Corey-Chaykovsky, Simmons-Smith, and metal catalyzed carbene attack on olefins. Under the current protocol, various alcohols are transformed into sulfone substituted cyclopropanes with excellent isolated yields and diastereoselectivities. This new reaction forms highly congested cyclopropane products with three new C–C bonds, three or two new chiral centers and one new quaternary carbon center. 22 examples of isolated substrates are given. Previously reported synthetic routes for similar substrates are all multi-step, linear routes that proceed with overall low yields and poor control of stereochemistry. Experimental mechanistic investigations suggest initial metal-catalyzed dehydrogenation of the alcohol substrate and catalyst independent stepwise attack of two equivalents of sulfone on the aldehyde under basic conditions. While the Ru(II) is only responsible for the initial dehydrogenation step, the rate of aldehyde formation is crucial to maintaining the right balance of intermediates needed to afford the cyclopropane product.

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Visible Light-Induced Sulfonylation/Arylation of Styrenes in a Double Radical Three-Component Photoredox Reaction

10.26434/chemrxiv.7722020.v1 ◽

2019 ◽

Author(s):

Benjamin Lipp ◽

Lisa Marie Kammer ◽

Murat Kucukdisli ◽

Adriana Luque ◽

Jonas Kühlborn ◽

...

Keyword(s):

Visible Light ◽

Radical Formation ◽

Three Component Reaction ◽

Broad Variety ◽

Styrene Derivatives ◽

Mechanistic Investigations

Simultaneous sulfonylation/arylation of styrene derivatives is achieved in a photoredox-catalyzed three-component reaction using visible light. A broad variety of difunctionalized products is accessible in mostly excellent yields and high diastereoselectivity. The developed reaction is scalable and suitable for the modification of styrene-functionalized biomolecules. Mechanistic investigations suggest the transformation to be operating through a designed sequence of radical formation and radical combination.<br>

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