The Stille Reaction, 38 Years Later

Cordovilla, Carlos; Bartolomé, Camino; Martínez‐Ilarduya, Jesús M.; Espinet, Pablo

doi:10.1021/acscatal.5b00448

Cited by 372 publications

(269 citation statements)

References 139 publications

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“…Prompted by our interest in CÀOf unctionalization, [4c, 5] we questioned whether an umpolung strategy could be designed to convert electrophilic aryl esters into nucleophilic organotin reagents,superb reaction intermediates for subsequent C À Sn cleavage (Scheme 1b). [7] Not surprisingly,t he MKS reaction is frequently used in the total synthesis of natural products [8] or for preparing densely functionalized polyheterocyclic cores, [9] privileged motifs in aw ide variety of pharmaceuticals, which are not particularly trivial to assemble by classical cross-coupling reactions. [7] Not surprisingly,t he MKS reaction is frequently used in the total synthesis of natural products [8] or for preparing densely functionalized polyheterocyclic cores, [9] privileged motifs in aw ide variety of pharmaceuticals, which are not particularly trivial to assemble by classical cross-coupling reactions.…”

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confidence: 99%

Ni‐Catalyzed Stannylation of Aryl Esters via C−O Bond Cleavage

Martı́n

2017

Angewandte Chemie

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confidence: 99%

Ni‐Catalyzed Stannylation of Aryl Esters via C−O Bond Cleavage

Martı́n

2017

Angewandte Chemie

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“…Interestingly, we found that arylstannanes and arylsilanes were inert under our reaction conditions both with and without added equivalents of fluoride, affording the opportunity for orthogonal cross coupling. 14 …”

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Palladium‐Catalyzed Defluorinative Coupling of 1‐Aryl‐2,2‐Difluoroalkenes and Boronic Acids: Stereoselective Synthesis of Monofluorostilbenes

2016

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The palladium-catalyzed defluorinative coupling of 1-aryl-2,2-difluoroalkenes with boronic acids is described. Broad functional group tolerance arises from a redox-neutral process via a Pd(II) active species that is proposed to undergo a β-fluoride elimination to afford the products. The monofluorostilbene products were formed with excellent diastereoselectivity (≥50:1) in all cases, which is critical, as traditional chromatographic techniques often fail to separate monofluoroalkene isomers. As a demonstration of this method’s unique combination of reactivity and functional group tolerance, a Gleevec© analogue using a monofluorostilbene as an amide isostere was synthesized.

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“…Highly substituted and functionalised cyclobutenediones can be prepared under mild and neutral reaction conditions to form carbon-carbon bonds (Stille coupling) [133]. A novel free radical approach involves using mono-and dialkyl-substituted cyclobutenediones has received much attention for its importance as synthetic precursors [96].…”

Section: Figure 35 Synthesis Of Phosphonic Acid Squaramidementioning

confidence: 99%

Squaryl Molecular Metaphors – Application to Rational Drug Design and Imaging Agents

Kitson¹

2017

J Diagn Imaging Ther

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Molecular Metaphors is the application of squaryl building blocks towards creative functional group chemistry to produce lead compounds and imaging agents. This strategy is applied to rational drug design and to various imaging agents that would normally contain conventional functional group chemistry. These, include carboxylic acids, α-amino acids, peptide bonds and phosphonates. Moreover, the squaryl metaphor is a precursor to complex organic molecules involving functional group interchange (FGI) and rearrangements. This article discusses the application of these metaphors in the area of neurochemistry, especially NMDA receptors. An important area of drug design is the inhibition of angiotensin II enzyme by the use of losartan. This commercial drug contains a tetrazole moiety that can be modified using the squaryl group to give a semisquarate derivative. These concepts can extend to the semisquarate of ibuprofen. Moreover, a discussion on peptidomimetics regarding the substitution of the peptide bond for squaramide allows for a change in the biological properties due to modification at the peptide bond. Furthermore, the topic on how squaryl metaphors can be exploited primarily by the central 1,3-hydroxyamide sequence to the generation of a novel class of HIV protease inhibitors. Also, squaryl metaphors can be used to develop potential inhibitors of glutathione and novel anti-migraine drugs. The discussion continues on the design of anticancer drugs: in particular, a novel class of metalloproteases, including phosphonates for semisquaramides, leading to squaryl nucleosides. This review concludes with the application of squaryl metaphors in the design of positron emission tomography (PET) and magnetic resonance imaging (MRI) agents towards theranostics. describe the ability of individual functional chemical groups to mimic other moieties [2,3]. KeywordsErlenmeyer rationalised these concepts and categorised isosteres into atoms, ions and molecules based on the valence level of electrons [4]. A further understanding by Friedman led to the term bioisosterism to include all atoms and molecules that fit the broadest definition of isosteres [5]. This approach was independent of whether the drug was an agonist or an antagonist towards biological activity.Moreover, Thornber applied the term bioisosterism to include subunits, groups or molecules that possess physicochemical properties of similar biological effects [6]. Finally, in 1991 Burger widened the definition of bioisosteres to include compounds or groups that possess similar molecular shapes and volumes independent of agonists or antagonists [7]. REVIEW ARTICLE Squaryl KitsonThese bioisosteres would require approximately the same distribution of electrons and give a high probability of generating comparable physical properties such as hydrophobicity [8]. Currently, bioisosterism is one of the most useful tools to the medicinal chemist in rational drug design and in particular regarding the carboxylic acid bioisosteres [9]. The carboxylic acid functional ...

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The Stille Reaction, 38 Years Later

Cited by 372 publications

References 139 publications

Ni‐Catalyzed Stannylation of Aryl Esters via C−O Bond Cleavage

Ni‐Catalyzed Stannylation of Aryl Esters via C−O Bond Cleavage

Palladium‐Catalyzed Defluorinative Coupling of 1‐Aryl‐2,2‐Difluoroalkenes and Boronic Acids: Stereoselective Synthesis of Monofluorostilbenes

Squaryl Molecular Metaphors – Application to Rational Drug Design and Imaging Agents

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