Synthesis of Allyl Aryl Sulfones from Morita–Baylis–Hillman Adducts and Thiosulfonates
Simple and Efficient Synthesis of Allyl Sulfones through Cs2CO3-Mediated Radical Sulfonylation of Morita–Baylis–Hillman Adducts with Thiosulfonates: A. Shankar, Md. Waheed, R. Jannapu Reddy
SynOpen 2021, 5, 91–99, DOI: 10.1055/a-1422-9411
Allyl aryl sulfones are important intermediates in organic synthesis; furthermore, this structural unit is present as pharmacophore in a number of bioactive compounds, such as anti-cancer and anti-bacterial agents. For these reasons there is strong and continued interest in the development of effective and straightforward methods for accessing diversely functionalized allyl aryl sulfones. Recently, the group of Dr. Raju Jannapu Reddy from the University College of Science, Osmania University (Hyderabad, India) reported a novel and versatile strategy for synthesizing the title compounds.
Dr. Reddy said: “A simple and efficient radical sulfonylation of Morita–Baylis–Hillman (MBH) allyl bromides/acetates with thiosulfonates in the presence of Cs2CO3 to access a range of (hetero)aryl/alkyl allyl sulfones in good to high yields. Various aryl, heteroaryl, alkenyl and alkyl MBH bromides/acetates and aryl/heteroaryl thiosulfonates were tolerated and reliable in scaled-up synthesis. It is worth noting that some of these allyl sulfones show activity against cancer and abnormal cell proliferation activity.”