2018
DOI: 10.1039/c8gc01488d
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Carbene-catalyzed aerobic oxidation of isoquinolinium salts: efficient synthesis of isoquinolinones

Abstract: A mild and environmentally friendly carbene-catalyzed aerobic oxidation of isoquinolinium salts was successfully realized.

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Cited by 64 publications
(30 citation statements)
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“…Recently, Fu and co‐workers have reported visible‐light‐mediated aerobic oxidation of N ‐alkyl pyridinium salts to synthesize quinolones and isoquinolones, [10] and Huang et al. disclosed carbene catalyzed aerobic oxidation of isoquinoline salt for the synthesis of isoquinolinones [11] are notable examples of this field.…”
Section: Introductionmentioning
confidence: 99%
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“…Recently, Fu and co‐workers have reported visible‐light‐mediated aerobic oxidation of N ‐alkyl pyridinium salts to synthesize quinolones and isoquinolones, [10] and Huang et al. disclosed carbene catalyzed aerobic oxidation of isoquinoline salt for the synthesis of isoquinolinones [11] are notable examples of this field.…”
Section: Introductionmentioning
confidence: 99%
“…[7d-e] Moreover, the Lee group reported aerobic α-oxidation of N-substituted tetrahydroisoquinolines to dihydroisoquinolones using eosin Y as a photocatalyst, [8] and Yang et al developed iodine catalyzed N-alkylation and amidation cascade to obtain isoquinolin-1(2H)-one. [9] Recently, Fu and coworkers have reported visible-light-mediated aerobic oxidation of N-alkyl pyridinium salts to synthesize quinolones and isoquinolones, [10] and Huang et al disclosed carbene catalyzed aerobic oxidation of isoquinoline salt for the synthesis of isoquinolinones [11] are notable examples of this field.…”
Section: Introductionmentioning
confidence: 99%
“…As part of our ongoing interest in organocatalysis, [5] on the basis of our previous work on carbene‐activated aldimines or iminiums, [4h,i,o] we planned to design a new type of aldimine containing a nucleophile moiety. We envisaged that this functionalized aldimine could be used as a new dipole via reverse polarity of the imine moiety to form an aza ‐Breslow intermediate, followed by its oxidation.…”
Section: Introductionmentioning
confidence: 99%
“…On the basis of Bringmann's pioneering work 41,42 , and the recent advance in constructing axially chiral backbones by ring opening of conformationally labile bridged biaryls [44][45][46][47][48] , we envisaged that the N-electron-withdrawing group configurationally labile biaryl lactams with an inherent torsional strain might act as suitable substrates for activation of amide C-N bonds, promoted by a bifunctional organocatalyst. According to our understanding of organocatalysis [49][50][51][52][53][54] , we herein present a strategy for direct organocatalytic asymmetric activation of N-sulfonyl amide C-N bonds promoted by a bifunctional organocatalyst under mild reaction conditions. We developed a straightforward catalytic asymmetric method for the synthesis of a structurally diverse set of axially chiral biaryl amino acids.…”
mentioning
confidence: 99%