Synthesis of 1‐Aryl‐β‐Carbolines via a Pd‐Catalyzed Oxidative Pictet‐Spengler Reaction/Aromatization Cascade Using Benzylic Alcohols in Water DOI Open Access
Masakazu Kobayashi, Hidemasa Hikawa,

Tomokatsu Enda

et al.

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 3, 2025

Abstract We report a Pd‐catalyzed oxidative Pictet‐Spengler reaction/aromatization cascade utilizing readily available benzylic alcohols for the construction of 1‐aryl‐ β ‐carbolines in water. Conceptually, this novel one‐pot, three‐step approach involves an initial Pd(0)/sodium diphenylphosphinobenzene‐3‐sulfonate (TPPMS)‐catalyzed dehydrogenation alcohols, followed by cyclization situ generated aldehydes with tryptamines, and concludes DBU/air‐promoted aromatization, allowing rapid access to desired ‐carbolines. The π ‐benzylPd (II) catalytic system from Pd(0)/TPPMS was found be highly effective alcohol

Language: Английский

Synthesis of 1‐Aryl‐β‐Carbolines via a Pd‐Catalyzed Oxidative Pictet‐Spengler Reaction/Aromatization Cascade Using Benzylic Alcohols in Water DOI Open Access
Masakazu Kobayashi, Hidemasa Hikawa,

Tomokatsu Enda

et al.

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 3, 2025

Abstract We report a Pd‐catalyzed oxidative Pictet‐Spengler reaction/aromatization cascade utilizing readily available benzylic alcohols for the construction of 1‐aryl‐ β ‐carbolines in water. Conceptually, this novel one‐pot, three‐step approach involves an initial Pd(0)/sodium diphenylphosphinobenzene‐3‐sulfonate (TPPMS)‐catalyzed dehydrogenation alcohols, followed by cyclization situ generated aldehydes with tryptamines, and concludes DBU/air‐promoted aromatization, allowing rapid access to desired ‐carbolines. The π ‐benzylPd (II) catalytic system from Pd(0)/TPPMS was found be highly effective alcohol

Language: Английский

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