58426-17-8

Upstream product

• 103028-42-8 3-bromo-1H-indene 
• 108-98-5 thiophenol 
• 100-52-7 benzaldehyde 
• 5736-44-7 Indanon-⁽¹⁾-hydrazon 

Relevant academic research and scientific papers

General Synthesis of Alkenyl Sulfides by Palladium-Catalyzed Thioetherification of Alkenyl Halides and Tosylates

The cross-coupling reaction of alkenyl bromides with thiols catalyzed by palladium complexes derived from inexpensive dppf ligand is reported. These reactions occur under low catalyst loading and in high yields and display wide scope, including the coupling of bulky thiols and trisubstituted bromoolefins, and functional group tolerance. In addition, the thioetherification of less reactive chloroalkenes and, for the first time, alkenyl tosylates was accomplished using a catalyst generated from CyPFtBu alkylbisphosphine ligand.

Organic Syntheses with Transition Metal Complexes, 48. - Methyl Thiocarbene and Alkenyl Thiocarbene Chromium Complexes: Synthesis and Reactions

Thiocarbene chromium complexes (CO)5Cr=C(SR1)R (4: R = Me, Ph; R1 = c-C6H11, CH2CH=CH2, C2H5, C6H5) were readily obtained in up to 97 percent isolated yields from the corresponding ethoxycarbene chromium complexes 5a,b and thiols 6 in methanol in the presence of Na2CO3 as a catalyst.Reaction conditions, which lead to unfavorable side products, like thioacetals 8 and/or thioenol ether 10, are discussed.Methyl thiocarbene complexes 4b-d undergo a facile aldol condensation with the aromatic aldehydes 14 or 16 to give alkenyl thiocarbene complexes 15b-d and 17, respectively.The Cr=C bonds of 15 prove to be reactive towards the insertion of isocyanides or oxygen.Thus, on addition of two equivalents of the isocyanide 18 to 15d, 1-aza-1,2,4-pentatriene 20 is obtained.The oxidative decomposition of 15d on silica gel leads to the formation of thioester 25 and thioindene 26.Characteristic differences in the reactivity of thiocarbene complexes and ethoxycarbene complexes are discussed.