Synthesis of organotrialkylstannanes. The reaction between organic halides and hexaalkyldistannanes in the presence of palladium complexes

Azizian, Hormoz; Eaborn, Colin; Pidcock, Alan

doi:10.1016/s0022-328x(00)84615-x

Cited by 197 publications

(80 citation statements)

References 9 publications

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“…The iodo substituent of compound 51 is easily exchanged by a trialkylstannyl group in the presence of a palladium catalyst. [22] The stannylated compound 55 can be reversibly transformed with radioactive iodine, which is generated in situ from radiolabelled NaI and chloramine T, to give the corresponding radiolabelled derivative of compound 51. [23] Additionally, compounds 56 (by using N-(3-bromopropyl)-phthalimide), 57, 60 and 61 were prepared according to Scheme 2.…”

Section: Resultsmentioning

confidence: 99%

Development of Novel 1,2,3,4‐Tetrahydroisoquinoline Derivatives and Closely Related Compounds as Potent and Selective Dopamine D₃ Receptor Ligands

et al. 2004

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Based on N-alkylated 1,2,3,4-tetrahydroisoquinoline derivatives, which are structurally related to the partial agonist BP 897, a series of novel, selective dopamine D3 receptor antagonists has been synthesised. Derivatisation included changes in the arylamide moiety and the tetrahydroisoquinoline substructure leading to compounds with markedly improved selectivities and affinities in the low nanomolar concentration range. From the 55 structures presented here, (E)-3-(4-iodophenyl)-N-(4-(1,2,3,4-tetrahydroisoquinolin-2-yl)butyl)acrylamide (51) has high affinity (Ki(hD3)=12 nM) and a 123-fold preference for the D3 receptor relative to the D2 receptor subtype. Its pharmacological profile offers the prospect of a novel radioligand as a tool for various dopamine D3-receptor-related in vitro and in vivo investigations.

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Section: Resultsmentioning

confidence: 99%

Development of Novel 1,2,3,4‐Tetrahydroisoquinoline Derivatives and Closely Related Compounds as Potent and Selective Dopamine D₃ Receptor Ligands

et al. 2004

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“…Therefore, mild palladium-catalyzed methods have to be used to form a boronate [192] or organostannane. [193] Base-promoted cyclizations in the presence of strong electron-withdrawing groups, such as imides, provide the rylenes in nearly quantitative yields, [189,191,194] while for materials without such groups oxidative cyclodehydrogenation of the coupled biaryls to the rylenes can be efficiently performed with aluminum trichloride or iron(iii) chloride. [195,196] Increasing the number of rylene units produces a red-shift in the emission so that terrylene (52) is a green emitter (l max = 573 nm) [195] and the emission maxima for the terrylenediimide (TDI, 53) [190] and quaterrylene (QDI, 54) [189,197] are at 650 and 760 nm, respectively ( Figure 6).…”

Section: Tuning the Properties Of Rylenesmentioning

confidence: 99%

The Chemistry of Organic Nanomaterials

2005

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The development of nanotechnology using organic materials is one of the most intellectually and commercially exciting stories of our times. Advances in synthetic chemistry and in methods for the investigation and manipulation of individual molecules and small ensembles of molecules have produced major advances in the field of organic nanomaterials. The new insights into the optical and electronic properties of molecules obtained by means of single-molecule spectroscopy and scanning probe microscopy have spurred chemists to conceive and make novel molecular and supramolecular designs. Methods have also been sought to exploit the properties of these materials in optoelectronic devices, and prototypes and models for new nanoscale devices have been demonstrated. This Review aims to show how the interaction between synthetic chemistry and spectroscopy has driven the field of organic nanomaterials forward towards the ultimate goal of new technology.

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“…The synthesis of 1-alkenylboronic acid pinacol esters via the palladium-catalyzed cross-coupling reaction of 1-alkenyl halides or triflates with bis(pinacolato)diboron [(Me 4 C 2 O 2 )B-B(O 2 C 2 Me 4 )] was carried out in toluene at 50 °C in the presence of potassium phenoxide (1.5 equivalents) and PdCl 2 (PPh 3 ) 2 •2PPh 3 (3 mol%).…”

Section: Division Of Molecular Chemistry Graduate School Of Engineermentioning

confidence: 99%

Synthesis of 1-Alkenylboronic Esters via Palladium-Catalyzed Cross-Coupling Reaction of Bis(pinacolato)diboron with 1-Alkenyl Halides and Triflates

Takahashi¹,

Takagi²,

Ishiyama³

et al. 2000

Chemistry Letters

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The synthesis of 1-alkenylboronic acid pinacol esters via the palladium-catalyzed cross-coupling reaction of 1-alkenyl halides or triflates with bis(pinacolato)diboron [(Me 4 C 2 O 2 )B-B(O 2 C 2 Me 4 )] was carried out in toluene at 50 °C in the presence of potassium phenoxide (1.5 equivalents) and PdCl 2 (PPh 3 ) 2 •2PPh 3 (3 mol%).The transition metal-catalyzed cross-coupling reaction of disilanes and distannanes is an elegant method for the synthses of organosilicone 1 and -tin 2 compounds directly from organic electrophiles, but the lack of suitable boron nucleophiles has limited this protocol. We have recently demonstrated the synthesis of arylboronates from aryl halides 3 or triflates 4 , and allylboronates from allyl acetates 5 via a palladium-catalyzed cross-coupling reaction of tetra(alkoxo)diborons. Very recently, Matsuda and Murata 6 found that pinacolborane (Me 4 C 2 O 2 )BH is an excellent boron-nucleophile for the palladium-catalyzed coupling reaction in the presence of triethylamine. Thus, tetra(alkoxo)diboron and pinacolborane are two nucleophiles now available for the boron cross-coupling reaction.In this paper, we report the palladium-catalyzed coupling reaction of bis(pinacolato)diboron (1) and 1-alkenyl halides or triflates, which provides a one-step procedure for the synthesis of 1-alkenylboronic esters from vinyl electrophiles (Eq. 1) 7 .

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Synthesis of organotrialkylstannanes. The reaction between organic halides and hexaalkyldistannanes in the presence of palladium complexes

Cited by 197 publications

References 9 publications

Development of Novel 1,2,3,4‐Tetrahydroisoquinoline Derivatives and Closely Related Compounds as Potent and Selective Dopamine D₃ Receptor Ligands

Development of Novel 1,2,3,4‐Tetrahydroisoquinoline Derivatives and Closely Related Compounds as Potent and Selective Dopamine D₃ Receptor Ligands

The Chemistry of Organic Nanomaterials

Synthesis of 1-Alkenylboronic Esters via Palladium-Catalyzed Cross-Coupling Reaction of Bis(pinacolato)diboron with 1-Alkenyl Halides and Triflates

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Synthesis of organotrialkylstannanes. The reaction between organic halides and hexaalkyldistannanes in the presence of palladium complexes

Cited by 197 publications

References 9 publications

Development of Novel 1,2,3,4‐Tetrahydroisoquinoline Derivatives and Closely Related Compounds as Potent and Selective Dopamine D3 Receptor Ligands

Development of Novel 1,2,3,4‐Tetrahydroisoquinoline Derivatives and Closely Related Compounds as Potent and Selective Dopamine D3 Receptor Ligands

The Chemistry of Organic Nanomaterials

Synthesis of 1-Alkenylboronic Esters via Palladium-Catalyzed Cross-Coupling Reaction of Bis(pinacolato)diboron with 1-Alkenyl Halides and Triflates

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Development of Novel 1,2,3,4‐Tetrahydroisoquinoline Derivatives and Closely Related Compounds as Potent and Selective Dopamine D₃ Receptor Ligands

Development of Novel 1,2,3,4‐Tetrahydroisoquinoline Derivatives and Closely Related Compounds as Potent and Selective Dopamine D₃ Receptor Ligands