2013
DOI: 10.1002/chem.201302290
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RhIII‐Catalyzed CH Activation: A Versatile Route towards Various Polycyclic Pyridinium Salts

Abstract: An efficient and convenient method for the synthesis of highly substituted polycyclic pyridinium salts from the reaction of various 2-aryl-pyridines and 2-aryl-sp(2) -nitrogen-atom-containing heterocycles with alkynes through rhodium(III)-catalyzed CH activation and annulation under an O2 atmosphere is described. A possible mechanism that involves the chelation-assisted CH activation of the 2-aryl-pyridine substrate, insertion of the alkyne, and reductive elimination is proposed. This mechanism was supported… Show more

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Cited by 97 publications
(53 citation statements)
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“…[54,55] In Huang's approach, ac ationic Rh III -complex, {Cp*Rh(H 2 O) 3 (OTf) 2 }( 1mol %), was used as the catalyst along with one equivalento fH OTf in MeOH at 120 8Cf or 22 hours under an O 2 atmosphere. [54,55] In Huang's approach, ac ationic Rh III -complex, {Cp*Rh(H 2 O) 3 (OTf) 2 }( 1mol %), was used as the catalyst along with one equivalento fH OTf in MeOH at 120 8Cf or 22 hours under an O 2 atmosphere.…”
Section: Synthesis Of Pyridinium and Polycyclic Pyridinium Saltsmentioning
confidence: 99%
“…[54,55] In Huang's approach, ac ationic Rh III -complex, {Cp*Rh(H 2 O) 3 (OTf) 2 }( 1mol %), was used as the catalyst along with one equivalento fH OTf in MeOH at 120 8Cf or 22 hours under an O 2 atmosphere. [54,55] In Huang's approach, ac ationic Rh III -complex, {Cp*Rh(H 2 O) 3 (OTf) 2 }( 1mol %), was used as the catalyst along with one equivalento fH OTf in MeOH at 120 8Cf or 22 hours under an O 2 atmosphere.…”
Section: Synthesis Of Pyridinium and Polycyclic Pyridinium Saltsmentioning
confidence: 99%
“…[6,7] In this field, the synthesis of nitrogen-containing heterocycles,l ike pyrrole, [8] pyridine, [9] and pyridinium salts, [10] has been developed extensively, whereas there are only af ew reports on the synthesis of oxygen-doped heterocycles like furan [11] and pyran. [6,7] In this field, the synthesis of nitrogen-containing heterocycles,l ike pyrrole, [8] pyridine, [9] and pyridinium salts, [10] has been developed extensively, whereas there are only af ew reports on the synthesis of oxygen-doped heterocycles like furan [11] and pyran.…”
mentioning
confidence: 99%
“…For instance, Cheng and co‐workers described rhodium‐catalyzed annulations of 2‐aryl pyridines and alkynes under O 2 atmosphere to prepare fluorescent pyridinium salts with potential applications in organic electronic devices 34. Similarly, Wang and co‐workers prepared polycyclic quinolinium cations in double C−H activation/annulation processes (Figure 5 I) 35.…”
Section: Metal‐catalyzed C−h Activation Reactionsmentioning
confidence: 99%