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.7b01602

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 › peer-review

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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
Pages (from-to)	3759-3762
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	14
Early online date	6 Jul 2017
DOIs	https://doi.org/10.1021/acs.orglett.7b01602
Publication status	Published - 21 Jul 2017

Keywords

boron substrates
Sonogashira coupling
Suzuki−Miyaura cross coupling
ribonucleosides

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10.1021/acs.orglett.7b01602Licence: CC BY 4.0

Buchanan-etal-OL-2017-Modular-step-efficient-palladium-catalyzed-cross-coupling-strategyFinal published version, 1.01 MBLicence: CC BY 4.0

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@article{481c2c1d58c246ccae042e617325c64c,

title = "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 = jul,

day = "21",

doi = "10.1021/acs.orglett.7b01602",

language = "English",

volume = "19",

pages = "3759--3762",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "14",

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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/

U2 - 10.1021/acs.orglett.7b01602

DO - 10.1021/acs.orglett.7b01602

M3 - Article

C2 - 28682638

SN - 1523-7060

VL - 19

SP - 3759

EP - 3762

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

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

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Industrial Case Account 2014 | Buchanan, Helena Stubbe

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

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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 | Buchanan, Helena Stubbe

Industrial Case Account 2014

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Data for "Modular, Step-Efficient Palladium-Catalyzed Cross-Coupling Strategy To Access C6-Heteroaryl 2‑Aminopurine Ribonucleosides"

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

Cite this