Modular, step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides

Helena S. Buchanan, Steven M. Pauff, Tilemachos D. Kosmidis, Andrea Taladriz-Sender, Olivia I. Rutherford, Marine Z. C. Hatit, Sabine Fenner, Allan J. B. Watson, Glenn A. Burley

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Two Pd-catalyzed methods to access 6-heteroaryl 2-aminopurine ribonucleosides from 6-chloroguanosine are described. First, Pd-132-catalyzed Suzuki-Miyaura cross-coupling using a series of boron substrates and 6-chloroguanosine forms 6-heteroaryl-2-aminopurines in a single step. The versatility of 6-chloroguanosine is further demonstrated using a modified Sonogashira coupling employing potassium iodide as an additive. Finally, the utility of the 6-alkynyl-2-aminopurine ribonucleoside as a dipolarophile in [3 + 2] cycloadditions is presented, affording triazoles and isoxazoles when reacted with azide and isonitrile 1,3-dipoles, respectively.

LanguageEnglish
Pages3759-3762
Number of pages4
JournalOrganic Letters
Volume19
Issue number14
Early online date6 Jul 2017
DOIs
Publication statusPublished - 21 Jul 2017

Fingerprint

2-Aminopurine
potassium iodides
Ribonucleosides
cross coupling
Palladium
cycloaddition
versatility
palladium
boron
dipoles
Isoxazoles
Potassium Iodide
Triazoles
Boron
Azides
Cycloaddition
Cycloaddition Reaction
Substrates

Keywords

  • boron substrates
  • Sonogashira coupling
  • Suzuki−Miyaura cross coupling
  • ribonucleosides

Cite this

Buchanan, Helena S. ; Pauff, Steven M. ; Kosmidis, Tilemachos D. ; Taladriz-Sender, Andrea ; Rutherford, Olivia I. ; Hatit, Marine Z. C. ; Fenner, Sabine ; Watson, Allan J. B. ; Burley, Glenn A. / Modular, step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides. In: Organic Letters. 2017 ; Vol. 19, No. 14. pp. 3759-3762.
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abstract = "Two Pd-catalyzed methods to access 6-heteroaryl 2-aminopurine ribonucleosides from 6-chloroguanosine are described. First, Pd-132-catalyzed Suzuki-Miyaura cross-coupling using a series of boron substrates and 6-chloroguanosine forms 6-heteroaryl-2-aminopurines in a single step. The versatility of 6-chloroguanosine is further demonstrated using a modified Sonogashira coupling employing potassium iodide as an additive. Finally, the utility of the 6-alkynyl-2-aminopurine ribonucleoside as a dipolarophile in [3 + 2] cycloadditions is presented, affording triazoles and isoxazoles when reacted with azide and isonitrile 1,3-dipoles, respectively.",
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Modular, step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides. / Buchanan, Helena S.; Pauff, Steven M.; Kosmidis, Tilemachos D.; Taladriz-Sender, Andrea; Rutherford, Olivia I.; Hatit, Marine Z. C.; Fenner, Sabine; Watson, Allan J. B.; Burley, Glenn A.

In: Organic Letters, Vol. 19, No. 14, 21.07.2017, p. 3759-3762.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Modular, step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides

AU - Buchanan, Helena S.

AU - Pauff, Steven M.

AU - Kosmidis, Tilemachos D.

AU - Taladriz-Sender, Andrea

AU - Rutherford, Olivia I.

AU - Hatit, Marine Z. C.

AU - Fenner, Sabine

AU - Watson, Allan J. B.

AU - Burley, Glenn A.

PY - 2017/7/21

Y1 - 2017/7/21

N2 - Two Pd-catalyzed methods to access 6-heteroaryl 2-aminopurine ribonucleosides from 6-chloroguanosine are described. First, Pd-132-catalyzed Suzuki-Miyaura cross-coupling using a series of boron substrates and 6-chloroguanosine forms 6-heteroaryl-2-aminopurines in a single step. The versatility of 6-chloroguanosine is further demonstrated using a modified Sonogashira coupling employing potassium iodide as an additive. Finally, the utility of the 6-alkynyl-2-aminopurine ribonucleoside as a dipolarophile in [3 + 2] cycloadditions is presented, affording triazoles and isoxazoles when reacted with azide and isonitrile 1,3-dipoles, respectively.

AB - Two Pd-catalyzed methods to access 6-heteroaryl 2-aminopurine ribonucleosides from 6-chloroguanosine are described. First, Pd-132-catalyzed Suzuki-Miyaura cross-coupling using a series of boron substrates and 6-chloroguanosine forms 6-heteroaryl-2-aminopurines in a single step. The versatility of 6-chloroguanosine is further demonstrated using a modified Sonogashira coupling employing potassium iodide as an additive. Finally, the utility of the 6-alkynyl-2-aminopurine ribonucleoside as a dipolarophile in [3 + 2] cycloadditions is presented, affording triazoles and isoxazoles when reacted with azide and isonitrile 1,3-dipoles, respectively.

KW - boron substrates

KW - Sonogashira coupling

KW - Suzuki−Miyaura cross coupling

KW - ribonucleosides

UR - http://strathprints.strath.ac.uk/61590/

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JO - Organic Letters

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JF - Organic Letters

SN - 1523-7060

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