Simple Methodology for Heck Arylation at C‐8 of Adenine Nucleosides

Lagisetty, Pallavi; Zhang, Li; Lakshman, Mahesh K.

doi:10.1002/adsc.200700418

Cited by 19 publications

(13 citation statements)

References 31 publications

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“…26 The vial was flushed with nitrogen gas and sealed with a Teflon-lined cap. The reaction mixture was stirred at 100 °C for 15 h, then diluted with EtOAc (10 mL), and washed with water and brine.…”

Section: Methodsmentioning

confidence: 99%

Stereoselective Synthesis of Conjugated Fluoro Enynes

Kumar

Zajc

2012

J. Org. Chem.

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Metalation-electrophilic fluorination of TMS- and TIPS-protected 1,3-benzothiazol-2-yl (BT) propargyl sulfones gave corresponding BT fluoropropargyl sulfones, Julia-Kocienski reagents for the synthesis of fluoro enynes. Both reagents reacted with aldehydes under mild DBU, or LHMDS-mediated conditions, giving high yields of conjugated fluoro enynes with E- stereoselectivity. In comparison to DBU-mediated reactions, stereoselectivity was higher in low-temperature LHMDS-mediated reactions. Two ketones were shown to react as well, using LHMDS as base. In situ removal of the TMS group gave terminal conjugated 2-fluoro 1,3-enynes. Synthetic utility of the fluoro enynes was demonstrated by conversion to internal alkynes and to stereoisomeric fluoro dienes via Sonogashira and Heck couplings.

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Section: Methodsmentioning

confidence: 99%

Stereoselective Synthesis of Conjugated Fluoro Enynes

Kumar

Zajc

2012

J. Org. Chem.

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“…The optimized conditions (Pd/CuI/ t BuOLi) were applicable for the selective alkenylation of caffeine, benzimidazole and other aromatic azole heterocycles [45,46]. These are significant developments since it was reported that 8-bromoadenosine was not a good substrate for Mizoroki-Heck reaction [47] making modification at 8 position via direct functionalization of C8-H bond a desirable transformation.…”

Section: Direct Activation Of C8-h Bond In Purine and Purine Nuclementioning

confidence: 99%

Modification of Purine and Pyrimidine Nucleosides by Direct C-H Bond Activation

Liang

Wnuk

2015

Molecules

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Transition metal-catalyzed modifications of the activated heterocyclic bases of nucleosides as well as DNA or RNA fragments employing traditional cross-coupling methods have been well-established in nucleic acid chemistry. This review covers advances in the area of cross-coupling reactions in which nucleosides are functionalized via direct activation of the C8-H bond in purine and the C5-H or C6-H bond in uracil bases. The review focuses on Pd/Cu-catalyzed couplings between unactivated nucleoside bases with aryl halides. It also discusses cross-dehydrogenative arylations and alkenylations as well as other reactions used for modification of nucleoside bases that avoid the use of organometallic precursors and involve direct C-H bond activation in at least one substrate. The scope and efficiency of these coupling reactions along with some mechanistic considerations are discussed.

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“…In the realm of biological chemistry, in 2008, Lagisetty et al [46] reported for the first time a simple method for the arylation at C-8 of adenine nucleosides. The motivation for this investigation was the observation that substitution at the C-8 position can influence the syn-anti conformational equilibrium around the glycosidic bond or produce structural factors that can influence enzymatic recognition.…”

Section: Arylations With the Heck-mizoroki Reactionmentioning

confidence: 99%

Cross‐Coupling Arylations: Precedents and Rapid HistoricalReview of the Field

2014

Catalytic Arylation Methods

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Simple Methodology for Heck Arylation at C‐8 of Adenine Nucleosides

Abstract: A simple method for the arylation of 8-vinyladenine nucleoside derivatives is reported. With a broad set of aryl iodides and bromides, the reaction is catalyzed by the simple combination palladium acetate/trisA

Cited by 19 publications

References 31 publications

Stereoselective Synthesis of Conjugated Fluoro Enynes

Stereoselective Synthesis of Conjugated Fluoro Enynes

Modification of Purine and Pyrimidine Nucleosides by Direct C-H Bond Activation

Cross‐Coupling Arylations: Precedents and Rapid HistoricalReview of the Field

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