Correction to "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

doi:10.1021/acs.orglett.7b02273

Correction to "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

Pure And Applied Chemistry

Research output: Contribution to journal › Article

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.

Language	English
Number of pages	1
Journal	Organic Letters
Volume	19
Issue number	14
DOIs	10.1021/acs.orglett.7b02273
Publication status	Published - 2 Aug 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, H. S., Pauff, S. M., Kosmidis, T. D., Taladriz-Sender, A., Rutherford, O. I., Hatit, M. Z. C., ... Burley, G. A. (2017). Correction to "Modular, step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides". Organic Letters, 19(14). https://doi.org/10.1021/acs.orglett.7b02273

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. / Correction to "Modular, step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides". In: Organic Letters. 2017 ; Vol. 19, No. 14.

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title = "Correction to {"}Modular, step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides{"}",

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.",

keywords = "boron substrates, Sonogashira coupling, Suzuki−Miyaura cross coupling, ribonucleosides",

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

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month = "8",

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doi = "10.1021/acs.orglett.7b02273",

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Buchanan, HS, Pauff, SM, Kosmidis, TD, Taladriz-Sender, A, Rutherford, OI, Hatit, MZC, Fenner, S, Watson, AJB & Burley, GA 2017, 'Correction to "Modular, step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides"' Organic Letters, vol. 19, no. 14. https://doi.org/10.1021/acs.orglett.7b02273

Correction to "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, 02.08.2017.

Research output: Contribution to journal › Article

TY - JOUR

T1 - Correction to "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 - 2017/8/2

Y1 - 2017/8/2

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/61338/

U2 - 10.1021/acs.orglett.7b02273

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M3 - Article

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JO - Organic Letters

T2 - Organic Letters

JF - Organic Letters