Modular, Step-Efficient Palladium-Catalyzed Cross-Coupling Strategy To Access C6-Heteroaryl 2-Aminopurine Ribonucleosides | Zendy

Helena S. Buchanan | Zendy; Steven M. Pauff | Zendy; Tilemachos D. Kosmidis | Zendy; Andrea TaladrizSender | Zendy; Olivia I. Rutherford | Zendy; Marine Z. C. Hatit | Zendy; Sabine Fenner | Zendy; Allan J. B. Watson | Zendy; Glenn A. Burley | Zendy

Open Access

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

Author(s) -

Helena S. Buchanan,

Steven M. Pauff,

Tilemachos D. Kosmidis,

Andrea TaladrizSender,

Olivia I. Rutherford,

Marine Z. C. Hatit,

Sabine Fenner,

Allan J. B. Watson,

Glenn A. Burley

Publication year - 2017

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b01602

Subject(s) - chemistry , palladium , catalysis , modular design , combinatorial chemistry , coupling (piping) , stereochemistry , organic chemistry , computer science , programming language , mechanical engineering , engineering

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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