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Tuning reactivity and site selectivity of simple arenes in C-H activation: ortho-arylation of anisoles via arene-metal π-complexation.

Ricci P, Krämer K, Larrosa I - J. Am. Chem. Soc. (2014)

Bottom Line: Current approaches to achieve site selectivity in the C-H activation of arenes involve the use of directing groups or highly electron-poor arenes.In contrast, simple arenes, such as anisole, are characterized by poor reactivity and selectivity.This mild methodology can be used for the late stage functionalization of bioactive compounds containing the anisole motif, allowing the construction of novel organic scaffolds with few synthetic steps.

View Article: PubMed Central - PubMed

Affiliation: School of Biological and Chemical Sciences, Queen Mary University of London , Joseph Priestley Building, Mile End Road, E1 4NS, London, U.K.

ABSTRACT
Current approaches to achieve site selectivity in the C-H activation of arenes involve the use of directing groups or highly electron-poor arenes. In contrast, simple arenes, such as anisole, are characterized by poor reactivity and selectivity. We report that π-complexation to a Cr(CO)3 unit enhances the reactivity of anisoles providing an unprecedented ortho-selective arylation. This mild methodology can be used for the late stage functionalization of bioactive compounds containing the anisole motif, allowing the construction of novel organic scaffolds with few synthetic steps.

No MeSH data available.


Scope of the Direct Arylation of Complex 1k with Iodoarenes 2a–oReactions carried out on a 0.5mmol scale with respect to the limiting reagent. Yields are of isolatedproduct. b Performed with 2.0 equiv of 2 for 40 h.
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sch3: Scope of the Direct Arylation of Complex 1k with Iodoarenes 2a–oReactions carried out on a 0.5mmol scale with respect to the limiting reagent. Yields are of isolatedproduct. b Performed with 2.0 equiv of 2 for 40 h.


Tuning reactivity and site selectivity of simple arenes in C-H activation: ortho-arylation of anisoles via arene-metal π-complexation.

Ricci P, Krämer K, Larrosa I - J. Am. Chem. Soc. (2014)

Scope of the Direct Arylation of Complex 1k with Iodoarenes 2a–oReactions carried out on a 0.5mmol scale with respect to the limiting reagent. Yields are of isolatedproduct. b Performed with 2.0 equiv of 2 for 40 h.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4379957&req=5

sch3: Scope of the Direct Arylation of Complex 1k with Iodoarenes 2a–oReactions carried out on a 0.5mmol scale with respect to the limiting reagent. Yields are of isolatedproduct. b Performed with 2.0 equiv of 2 for 40 h.
Bottom Line: Current approaches to achieve site selectivity in the C-H activation of arenes involve the use of directing groups or highly electron-poor arenes.In contrast, simple arenes, such as anisole, are characterized by poor reactivity and selectivity.This mild methodology can be used for the late stage functionalization of bioactive compounds containing the anisole motif, allowing the construction of novel organic scaffolds with few synthetic steps.

View Article: PubMed Central - PubMed

Affiliation: School of Biological and Chemical Sciences, Queen Mary University of London , Joseph Priestley Building, Mile End Road, E1 4NS, London, U.K.

ABSTRACT
Current approaches to achieve site selectivity in the C-H activation of arenes involve the use of directing groups or highly electron-poor arenes. In contrast, simple arenes, such as anisole, are characterized by poor reactivity and selectivity. We report that π-complexation to a Cr(CO)3 unit enhances the reactivity of anisoles providing an unprecedented ortho-selective arylation. This mild methodology can be used for the late stage functionalization of bioactive compounds containing the anisole motif, allowing the construction of novel organic scaffolds with few synthetic steps.

No MeSH data available.