Palladium-catalyzed C–H bond functionalization of C6-arylpurines

Guo, Hai‐Ming; Rao, Wei‐Hao; Niu, Hong‐Ying; Jiang, Lili; Meng, Guangrong; Jin, Jia-Jia; Yang, Xi; Qu, Gui‐Rong

doi:10.1039/c1cc11135c

Cited by 57 publications

(18 citation statements)

References 53 publications

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“…18 There, oxidation of 6-phenyl-9-(2,3,5-tri- O -acetyl- β -D-ribofuranosyl)purine gave mono- as well as diacetoxylated products in a ~2.1:1 ratio (combined 77% yield). 18 This substrate, being a ribonucleoside and bearing electron-withdrawing acetate protecting groups on the saccharide, proved to be relatively stable in acetic acid at 120 °C. These conditions, however, are likely to be incompatible with more sensitive substrates.…”

Section: Results and Discissionmentioning

confidence: 99%

“…18 Thus, palladated dimers such as 10 , which can potentially form in the reaction, are competent in catalyzing the oxidation reaction. The plausible involvement of 10 in the catalytic cycle is shown in Scheme 1.…”

Section: Results and Discissionmentioning

confidence: 99%

“… c Under conditions reported in ref 18 (5 mol % of Pd(OAc) 2 , 1.5 mol equiv of PhI(OAc) 2 , Ac 2 O, AcOH, 120 °C, 5 h). …”

Section: Figurementioning

confidence: 99%

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Purinyl N1-Directed Aromatic C–H Oxidation in 6-Arylpurines and 6-Arylpurine Nucleosides

et al. 2013

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Palladium-catalyzed C–H bond activation and oxidation of C6 arylpurines as well as C6 arylpurine nucleosides can be accomplished using Pd(OAc)2/PhI(OAc)2 in CH3CN. Despite the presence of four nitrogen atoms in the purine moiety as well as the polyoxygenated saccharide and a labile glycosidic bond in the nucleosides, these reactions can be effectively conducted. Notably, the generally more labile 2′-deoxyribonucleosides also undergo reaction. The reaction conditions can be tuned to yield either monoacetoxylated or diacetoxylated products predominantly. In the course of these investigations, a dimeric PdII-containing cyclopalladated C6 naphthylpurine derivative has been obtained and crystallographically characterized. This compound is competent in catalyzing the oxidization with PhI(OAc)2, indicating its plausible intermediacy in the chemistry. The X-ray structure of a monoacetoxylated product from this reaction has also been obtained.

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Section: Results and Discissionmentioning

confidence: 99%

Section: Results and Discissionmentioning

confidence: 99%

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Purinyl N1-Directed Aromatic C–H Oxidation in 6-Arylpurines and 6-Arylpurine Nucleosides

et al. 2013

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“…ortho ‐Alkoxylation of 9‐butyl‐6‐phenylpurine and 9‐benzyl‐6‐phenylpurine has been performed with Pd(OAc) 2 /PhI(OAc) 2 at 100 °C [Equation ].…”

Section: Purinyl Coordinating Groupsmentioning

confidence: 99%

Dehydrogenative (Hetero)arene Alkoxylations Triggered by Pd^II‐Catalyzed C(sp²)–H Activation and Coordinating Substituent: Pd^II,III or Pd^IV Complex as Key Intermediate?

Bras

Мuzart

2017

Eur J Org Chem

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This review summarizes the intermolecular PdII‐catalyzed dehydrogenation procedures leading to regioselective coupling of alcohols with (hetero)arenes bearing tethered coordinating groups. Unusual oxidative conditions of catalyst regeneration are required, and the optimum oxidant varies with the substrate. Emphasis is placed on the mechanism of these intriguing reactions. Either PdII–Pd0 or PdII–PdIV redox catalytic cycles, possibly with PdIII intermediates, could be involved, depending on the directing group.

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“…36 It has recently been quantitatively shown that 2′-deoxyribonucleosides are substantially more labile as compared to the ribosyl counterparts. For example, the t 1/2 for the deglycosylation of adenosine in 0.1 M HCl is 11 days at 37 °C.…”

Section: Purinyl N-directed C–h Bond Oxidation Using Pidamentioning

confidence: 99%

When nucleoside chemistry met hypervalent iodine reagents

Lakshman

Zajc

2017

Arkivoc

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There has been increasing use of hypervalent iodine reagents in the field of nucleoside chemistry. Applications span: (a) synthesis of nucleoside analogues with sulfur and seleno sugar surrogates, (b) synthesis of unusual carbocyclic and ether ring-containing nucleosides, (c) introduction of sulfur and selenium into pyrimidine bases of nucleosides and analogues, (d) synthesis of isoxazole and isoxazoline ring-containing nucleoside analogues, (e) involvement of purine ring nitrogen atoms for remote C–H bond oxidation, and (f) metal-catalyzed and uncatalyzed synthesis of benzimidazolyl purine nucleoside analogues by intramolecular C–N bond formation. This review offers a perspective on developments involving the use of hypervalent iodine reagents in the field of nucleoside chemistry that have appeared in the literature in the 2003–2017 time frame.

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Palladium-catalyzed C–H bond functionalization of C6-arylpurines

Cited by 57 publications

References 53 publications

Purinyl N1-Directed Aromatic C–H Oxidation in 6-Arylpurines and 6-Arylpurine Nucleosides

Purinyl N1-Directed Aromatic C–H Oxidation in 6-Arylpurines and 6-Arylpurine Nucleosides

Dehydrogenative (Hetero)arene Alkoxylations Triggered by Pd^II‐Catalyzed C(sp²)–H Activation and Coordinating Substituent: Pd^II,III or Pd^IV Complex as Key Intermediate?

When nucleoside chemistry met hypervalent iodine reagents

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Palladium-catalyzed C–H bond functionalization of C6-arylpurines

Cited by 57 publications

References 53 publications

Purinyl N1-Directed Aromatic C–H Oxidation in 6-Arylpurines and 6-Arylpurine Nucleosides

Purinyl N1-Directed Aromatic C–H Oxidation in 6-Arylpurines and 6-Arylpurine Nucleosides

Dehydrogenative (Hetero)arene Alkoxylations Triggered by PdII‐Catalyzed C(sp2)–H Activation and Coordinating Substituent: PdII,III or PdIV Complex as Key Intermediate?

When nucleoside chemistry met hypervalent iodine reagents

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Dehydrogenative (Hetero)arene Alkoxylations Triggered by Pd^II‐Catalyzed C(sp²)–H Activation and Coordinating Substituent: Pd^II,III or Pd^IV Complex as Key Intermediate?