Abstract
C–C bond formation is one of the most important implements in synthetic organic chemistry. In pursuit of effective synthetic routes functioning under greener pathways to achieve direct C–C bond formation, we report N-iodosuccinimide (NIS) as the most effective precatalyst among the N-halosuccinimides (NXSs) for the direct cross-coupling of benzyl alcohols with C-nucleophiles under solvent-free reaction conditions (SFRC). The protocol is metal-free, and air- and water-tolerant, providing a large-scale synthesis with almost quantitative yields.
Highlights
C–C bond formation is one of the most significant approaches for the synthesis of complex organic compounds such as pharmaceuticals and agrochemicals [1]
The coupling of diphenylmethanol 1 and 1,3-diphenylpropane-1,3-dione 2 was chosen as a model reaction to employ NIS as the catalyst in direct cross-coupling of β-diketones and alcohols and to study the effects of different reaction conditions
The impact of different solvents on the conversion of 1 with 2 was studied, where it seemed to be inconvenient for the conversion of 1 with 2, while solvent-free reaction conditions were critical for quantitative transformation, and the results are shown in the Supplementary Materials (Table S1)
Summary
C–C bond formation is one of the most significant approaches for the synthesis of complex organic compounds such as pharmaceuticals and agrochemicals [1]. Alcohols are readily available and one of the most abundant organic compounds Their employment for direct cross-coupling reactions with other partners is highly desirable, producing water as the only by-product, making the protocol environmentally benign. Since hydroxyl moieties are a weak leaving group, often an additional activation is unavoidable [2]. Solvent-free synthetic methods have attracted significant interest in laboratory synthesis and in the chemical industry due to their simplicity and cost-efficiency. With this in mind, it is becoming essential to develop efficient, selective, and environmentally benign catalytic systems for direct dehydrative
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