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

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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.

Original language	English
Number of pages	1
Journal	Organic Letters
Volume	19
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.7b02273
Publication status	Published - 2 Aug 2017

Keywords

boron substrates
Sonogashira coupling
Suzuki−Miyaura cross coupling
ribonucleosides

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10.1021/acs.orglett.7b02273Licence: CC BY 4.0

Buchanan-etal-OL-2017-Correction-to-modular-step-efficient-palladium-catalyzed-cross-coupling-strategyFinal published version, 223 KBLicence: CC BY 4.0

http://strathprints.strath.ac.uk/61338/

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Industrial Case Account 2014
McFarlane, A.
EPSRC (Engineering and Physical Sciences Research Council)
1/10/14 → 30/09/19
Project: Research - Studentship
Industrial Case Account 2013 | Rutherford, Olivia
Burley, G., Tomkinson, N. & Rutherford, O.
EPSRC (Engineering and Physical Sciences Research Council)
1/07/14 → 26/09/18
Project: Research Studentship Case - Internally allocated

Data for "Modular, Step-Efficient Palladium-Catalyzed Cross-Coupling Strategy To Access C6-Heteroaryl 2‑Aminopurine Ribonucleosides"
Buchanan, H. S. (Creator), University of Strathclyde, 18 Jan 2018
DOI: 10.15129/1ed57e7a-8fcb-4b99-b89b-88f19e987183
Dataset

1 Article

Modular, step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides
Buchanan, H. S., Pauff, S. M., Kosmidis, T. D., Taladriz-Sender, A., Rutherford, O. I., Hatit, M. Z. C., Fenner, S., Watson, A. J. B. & Burley, G. A., 21 Jul 2017, In: Organic Letters. 19, 14, p. 3759-3762 4 p.
Research output: Contribution to journal › Article › peer-review

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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.

@article{5dfd030b62264f149fc26f890f34c1c7,

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.}",

year = "2017",

month = aug,

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

language = "English",

volume = "19",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "14",

}

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 › peer-review

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

DO - 10.1021/acs.orglett.7b02273

M3 - Article

VL - 19

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 14

ER -

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

Abstract

Keywords

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Industrial Case Account 2014

Industrial Case Account 2013 | Rutherford, Olivia

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Research output

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

Cite this