A Highly Diastereoselective Pinacol Coupling Reaction of Aldehydes and Ketones Using Low-Valence Niobium Generated from Nb(V)

Arai, Shigeru; Sudo, Yukinori; Nishida, Atsushi

doi:10.1248/cpb.52.287

Cited by 20 publications

(6 citation statements)

References 6 publications

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“…Concerning acetophenone derivatives 1U and 1V (Table 6, entries 21 and 22), their very slow reactivitiescould be attributed to the difficulty in generating and stabilizing the ketyl radical on this aromatic ketone compared with aromatic aldehydes as previously described. [19] It is noteworthy that total selectivities and excess in dl isomer wereo btained with acetophenone derivatives.…”

Section: Scope Of the Reactionmentioning

confidence: 99%

First Pinacol Coupling in Emulsified Water: Key Role of Surfactant and Impact of Alternative Activation Technologies

Billamboz

Len

2015

ChemSusChem

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For the first time, the influence of surfactants on the radical pinacol coupling reaction is investigated. The rate and selectivity of this reductive C-C coupling are compared under three different activation technologies: thermal activation, microwave irradiation, and sonication. The use of IgepalCO520, a neutral surfactant, led to the successful conversion of aromatic or α,β-unsaturated aliphatic carbonyl compounds in moderate to excellent yield (55-90 %). An insight on the potential mechanism involved in the reaction is also proposed, based on microscopic observations and particle size measurement.

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Section: Scope Of the Reactionmentioning

confidence: 99%

First Pinacol Coupling in Emulsified Water: Key Role of Surfactant and Impact of Alternative Activation Technologies

Billamboz

Len

2015

ChemSusChem

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“…Arai and co-workers reported the use of low-valence niobium in the pinacol coupling of aldehydes and ketones furnishing the corresponding 1,2-diols [28]. The Nb(III) used was freshly generated in situ through the reduction reaction between NbCl 5 and zinc powder to subsequent coupling reaction.…”

Section: -Pinacol Couplingmentioning

confidence: 99%

Recent Applications of Niobium Catalysts in Organic Synthesis

Rocha¹

2006

MROC

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Niobium catalysts generally possess a good Lewis acidity and have received increased attention in recent years. The applications of niobium pentachloride as Lewis acid in organic synthesis have been recently reviewed. Since then, there has been an increasing number of examples on the use of niobium catalysts in organic reactions such as Biginelli reactions, Friedel-Crafts acylation and Sakurai-Hosomi reactions of acetals, Knoevenagel condensation, acetylation of alcohols and phenols, among others. Also, chiral niobium complexes have been reported to give high enantiomeric excesses in asymmetric Mannich-type reactions.In this review, recent applications of these versatile reagents in organic synthesis, including our own results, will be disclosed.

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“…Following pioneer works reported by Fitting, this reaction still finds many applications for constructing biologically important products or useful synthetic intermediates . Many batch methodologies for pinacol coupling reactions have been developed using low-valent metals in excess such as the Zn–Cu couple, Mg, Mn, Zn, In, Sm, Al, Ga, and other metals . Ti, V, or Zr complexes have also been widely used to promote this reaction .…”

Section: Introductionmentioning

confidence: 99%

Selective Pinacol-Coupling Reaction using a Continuous Flow System

et al. 2016

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The first continuous flow pinacol coupling reaction of carbonyl compounds was successfully achieved within only 2 min during a single pass through a cartridge filled with zinc(0). The optimized method allowed the efficient production of gram-scale value-added compounds with high productivity. The developed methodology is efficient for aromatic or α,β-unsaturated aldehydes but gives moderate results for more stable acetophenone derivatives. Moreover, the flow method displayed better results in terms of yield and selectivity in comparison to the corresponding batch methodology.

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A Highly Diastereoselective Pinacol Coupling Reaction of Aldehydes and Ketones Using Low-Valence Niobium Generated from Nb(V)

Cited by 20 publications

References 6 publications

First Pinacol Coupling in Emulsified Water: Key Role of Surfactant and Impact of Alternative Activation Technologies

First Pinacol Coupling in Emulsified Water: Key Role of Surfactant and Impact of Alternative Activation Technologies

Recent Applications of Niobium Catalysts in Organic Synthesis

Selective Pinacol-Coupling Reaction using a Continuous Flow System

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