Abstract
A TBHP-mediated dehydrogenative cross-oxidative-coupling approach has been developed for the synthesis of N-arylbenzamides from methylarenes and acetanilides. This cross-coupling method is free of transition metal catalysts and ligands, and no extra organic solvents are required, which make it an useful and attractive strategy for the straightforward construction of C–N bonds. Besides, this conversion is an important complement to the conventional C–N forming strategies.
Highlights
Amides have attracted more and more attention due to their extensive utilization in pharmaceutical and agrochemical applications [1,2,3], as well as for precursors in organic synthesis for the construction of natural products, polymers and organic materials [4,5,6]
We began by studying the reaction of toluene (1a) and acetanilide (2a) as model substrates to identify the optimal conditions (Table 1)
The results show that the reaction was completed after 24 h and led to the desired N-phenylbenzamide 3aa in 62% GC yield (Table 1, entry 2)
Summary
Amides have attracted more and more attention due to their extensive utilization in pharmaceutical and agrochemical applications [1,2,3], as well as for precursors in organic synthesis for the construction of natural products, polymers and organic materials [4,5,6]. We disclose a dehydrogenative C–N cross-oxidative-coupling reaction of methylarenes with acetanilides, using TBHP as an oxidant to afford N-arylamides in moderate to good yields (Scheme 1). We began by studying the reaction of toluene (1a) and acetanilide (2a) as model substrates to identify the optimal conditions (Table 1). To optimize the reaction time (Table 1, entries 1–3).
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