Nucleophilic Addition of Thiolate and Sulfinate Ions to in Situ-derived Nitrosoalkenes in Low Transition Temperature Mixtures

The environmental impact associated with chemical synthesis has recently posed severe and compelling demands for sustainable chemistry, and the development of cost-effective and environmentally benign reactions systems in place of volatile and harsh organic compounds represents an active field of research. A new generation of solvents emerged in the last decade as promising green media are: the Low-Transition-Temperature Mixtures (LTTMs). They can be prepared by mixing natural high-melting-point starting materials, which form a liquid by hydrogen-bond interactions.[1] In this communication we will discuss the potential benefits of using environmentally friendly, bio-based LTTMs (e.g. L-lactic acid/Choline Chloride) in direct nucleophilic addition of thiolates and sulfinates ions to in situ-derived nitrosoalkenes affording the corresponding sulfenylated or sulfonylated adducts respectively, in very good yield (up to >98%, Scheme 1).[2] This methology offers the advantage of working at room temperature and under air in biodegradable and cost-effective reaction mixtures.