A General Method for Copper-Catalyzed Arene Cross-Dimerization

Do, Hien‐Quang; Daugulis, Olafs

doi:10.1021/ja2047717

Cited by 152 publications

(47 citation statements)

References 106 publications

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“…Recently, this copper‐catalyzed arylation was combined with an in situ iodination protocol in a one‐pot reaction, which constitutes a very general approach to cross‐couple electron‐poor (hetero)arenes with various electron‐rich heterocycles and benzene derivatives. With this methodology, good selectivities for the cross‐coupled over homo‐coupled products as well as excellent regioselectivies could be obtained (Scheme ) 21a…”

Section: Cc Bond Formationmentioning

confidence: 99%

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Beyond Directing Groups: Transition‐Metal‐Catalyzed CH Activation of Simple Arenes

Kuhl¹,

Hopkinson²,

et al. 2012

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The use of coordinating moieties as directing groups for the functionalization of aromatic C-H bonds has become an established tool to enhance reactivity and induce regioselectivity. Nevertheless, with regard to the synthetic applicability of C-H activation, there is a growing interest in transformations in which the directing group can be fully abandoned, thus allowing the direct functionalization of simple benzene derivatives. However, this approach requires the disclosure of new strategies to achieve reactivity and to control selectivity. In this review, recent advances in the emerging field of non-chelate-assisted C-H activation are discussed, highlighting some of the most intriguing and inspiring examples of induction of reactivity and selectivity.

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Section: Cc Bond Formationmentioning

confidence: 99%

“… Sequential iodination/cross‐coupling of electron‐deficient benzene derivatives developed by Daugulis and co‐workers 21a…”

Section: Cc Bond Formationmentioning

confidence: 99%

Beyond Directing Groups: Transition‐Metal‐Catalyzed CH Activation of Simple Arenes

Kuhl¹,

Hopkinson²,

et al. 2012

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“…First, the protocol using copper and cesium carbonate (2 equiv) at acetonitrile reflux for 24 h was applied; 13 no reaction was observed with either 0.2 or 0.4 equiv of transition metal (entries 1 and 2), in accordance with the results obtained in Table 1 (entries 8-11). It is interesting to notice that N-(4methoxy-2-pyridyl) pyrrole (3b') was not obtained either, allowing to discard both direct addition of copper azolates onto pyridines and conversion of 3a-I into 3a-I' by halogen loss followed by halogenation 16 at a different site.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of N-pyridyl azoles using a deprotometalation-iodolysis-N-arylation sequence and evaluation of their antiproliferative activity in melanoma cells

et al. 2016

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N-Arylation of pyrrole with 3-iodo-4-methoxypyridine was investigated by copper catalysis under different conditions. The best conditions, that proved to be protocol A (CuI, DMEDA or TMEDA, K 3 PO 4 , DMF at 110 °C) and above all protocol B (Cu 2 O, Cs 2 CO 3 , DMSO at 110 °C), were applied to the synthesis of various N-(methoxypyridyl) pyrroles, indoles and benzimidazoles. The behavior of the different iodinated methoxypyridines was rationalized by evaluating the partial positive charge on the carbon bearing iodine from the 1 H NMR chemical shift of the corresponding deiodinated substrates. The reaction was next connected with the deprotometalation-iodolysis step generating iodinated methoxypyridines: straight involvement of the crude iodo intermediates in pyrrole N-arylation afforded the expected N-(methoxypyridyl) pyrroles in good yields. Several synthesized N-(methoxypyridyl) azoles exerted low to moderate antiproliferative activity in A2058 melanoma cells.

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“…91 The reaction is believed to be a two-step process. In the first, fast step, one of the coupling partners undergoes iodination.…”

Section: C4–h-functionalizationmentioning

confidence: 99%

Recent advances in the C–H-functionalization of the distal positions in pyridines and quinolines

2015

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This review summarizes recent developments in the C–H-functionalization of the distal positions of pyridines, quinolines and related azaheterocycles. While the functionalization of the C2 position has been known for a long time and is facilitated by the proximity to N1, regioselective reactions in the distal positions are more difficult to achieve and have only emerged in the last decade. Recent advances in the transition metal-catalyzed distal C–H-functionalization of these synthetically-important azaheterocycles are discussed in detail, with the focus on the scope, site-selectivity and mechanistic aspects of the reactions.

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A General Method for Copper-Catalyzed Arene Cross-Dimerization

Cited by 152 publications

References 106 publications

Beyond Directing Groups: Transition‐Metal‐Catalyzed CH Activation of Simple Arenes

Beyond Directing Groups: Transition‐Metal‐Catalyzed CH Activation of Simple Arenes

Synthesis of N-pyridyl azoles using a deprotometalation-iodolysis-N-arylation sequence and evaluation of their antiproliferative activity in melanoma cells

Recent advances in the C–H-functionalization of the distal positions in pyridines and quinolines

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