Abstract
The reactive thiocarbonyl ylides belong to the less well-known class of the so-called ‘sulfur-centered 1,3-dipoles’. Only in recent years have the [2+3] cycloadditions with thiocarbonyl ylides been extensively explored, mainly as a useful method for the synthesis of three- and five-membered sulfur heterocycles. The goal of the present review is to demonstrate the potential of the 1,5-dipolar electrocyclization of properly substituted thiocarbonyl ylides as an alternative approach to syntheses of sulfur heterocycles such as 1,3- oxathiolanes, 1,3-thiazoles, 1,3-dithioles, and thiophenes. Thermal, as well as metal-catalyzed, generations of the reactive intermediates from diazo and thiocarbonyl precursors are summarized and discussed. The presented examples show the scope and limitations of this general but relatively scarcely-investigated reaction.
Keywords: Thiocarbonyl ylides, Electrocyclizations, Sulfur heterocycles
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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