Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.
نویسندگان
چکیده
Diarylmethylamines are of great interest due to their prevalence in pharmaceutical chemistry. As a result, new methods for their synthesis are in demand. Herein, we report a versatile protocol for the synthesis of diarylmethylamine derivatives involving palladium-catalyzed arylation of in situ generated 2-azaallyl anion intermediates. The 2-azaallyl anions are generated by reversible deprotonation of readily available aldimine and ketimine precursors. Importantly, the arylated aldimine and ketimine products do not undergo isomerization under the reaction conditions. Scale-up of the arylation and hydrolysis of the resulting products to furnish diarylmethylamines were also successfully performed.
منابع مشابه
Palladium-Catalyzed Regioselective Arylation of 1,1,3-Triaryl-2-azaallyl Anions with Aryl Chlorides
A regioselective arylation of 1,1,3-triaryl-2-azaallyl anions with aryl chlorides is described. The palladium-NIXANTPHOS-based catalyst affords diarylmethylamine derivatives in good yield and without product isomerization. A gram scale sequential one-pot ketimine synthesis/arylation protocol was also developed.
متن کاملPalladium catalyzed dehydrogenative arylation of coumarins: an unexpected switch in regioselectivity.
A new regioselective α-arylation of coumarins with unactivated simple arenes via a palladium-catalyzed twofold C-H functionalization is devised. This method offers an attractive new approach to synthesis of a wide variety of 3-arylcoumarins from readily accessible starting materials.
متن کاملEfficient synthesis of π-conjugated molecules incorporating fluorinated phenylene units through palladium-catalyzed iterative C(sp2)–H bond arylations
We report herein a two or three step synthesis of fluorinated π-conjugated oligomers through iterative C-H bond arylations. Palladium-catalyzed desulfitative arylation of heteroarenes allowed in a first step the synthesis of fluoroaryl-heteroarene units in high yields. Then, the next steps involve direct arylation with aryl bromides catalyzed by PdCl(C3H5)(dppb) to afford triad or tetrad hetero...
متن کاملPalladium-Catalyzed Regioselective 2-Carbethoxyethylation of 1H–Indoles By C-H Activation: One-Step Synthesis of Ethyl 2-(1H-Indol-2-Yl) Acetates
An efficient and convenient method was developed for the one-step synthesis of various substituted ethyl 2-(1H-indol-2-yl) acetates via a palladium-catalyzed regioselective cascade C-H activation reaction. Importantly, this practical approach can be carried out with readily accessible starting materials and exhibits excellent functional group compatibility. chemistry, methods for regioselective...
متن کاملPalladium-catalyzed olefination and arylation of 2-substituted 1,2,3-triazole N-oxides.
Two highly efficient protocols for the regioselective synthesis of 2-substituted 4-alkenyl- and 4-aryl-1,2,3-triazoles by the palladium-catalyzed C-H functionalization of 1,2,3-triazole N-oxides are reported. A possible pathway of direct alkenylation with 1-octene and vinyl acetate is discussed.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Chemical science
دوره 5 6 شماره
صفحات -
تاریخ انتشار 2014