Copper-free sonogashira coupling reaction using a trans-spanning 1,2-Bis(2-thienylethynyl)benzene ligand
Novel copper-free Sonogashira coupling reaction of aryl halides with terminal acetylenes proceeded in the presence of 1,2-bis(2-thienylethynyl) benzene (1) as a trans-bidentatable ligand.
Synthesis of alkylthio- and arylthioheteroarenes by regioselective grignard reaction of thiocyanatoheteroarenes
Treatment of thiocyanatoheteroarenes (1) with Grignard reagents (2) afforded alkylthio- or arylthioheteroarenes (3-6) in good yields. Grignard reagents regioselectively attacked the sulfur atom of the thiocyanato group owing to the metal-chelating effect of this group in combination with the hetero ring-nitrogen. 2-Thiocyanatopyridine (1a), 2-thiocyanatopyrimidine (1b), 2-thiocyanatobenzothiazole (1c), and 4-thiocyanatoquinazoline (1d) were converted into a variety of sulfides. Sulfides consisting of two heteroarenes linked by a sulfur atom were readily obtained by this method.
INTRODUCTION OF SULFUR IN COMPOUNDS WITH REACTIVE HALOGEN ATOMS VIA THE t-BUTYLTHIOLATE ANION
The preparation of t-butylthioethers from examples of halogen substituted heterocycles are described.S-Dealkylation of the t-butylthioethers readily takes place by pyrolyses with catalytic amounts of aluminum chloride or p-toluenesulfonic acid.
Becher, Jan,Lundsgaard, John
p. 131 - 138
(2007/10/02)
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