Insertion of Pt into CH and CS bonds of thiophene derivatives. The X-ray crystal structure of a thiaplatinacycle of 3,6-dimethylthieno[3,2-b]thiophene

Transition-metal mediated carbon–sulfur bond activation and transformations

“…The reactions of [Pt(PEt 3 ) 4 ] with 2,2 0 -bithiophene and 1-methyl-2-(2-thienyl)pyrrole afforded two types of products, i.e., thiaplatinacycles resulting from C-S insertion, and Pt(II) hydride arising from C-H insertion. 36 Remote activation of C-S bonds in alkylated benzothiophenes and dibenzothiophenes by metal coordination to a carbocyclic ring was achieved (eqn ( 8)). 37 For the C-S bond cleavage reactions of benzothiophenes, the metal of a highly coordinatively unsaturated nucleophilic metal fragment usually inserts into the C(vinyl)-S bond instead of inserting into the stronger C(aryl)-S bond of the free benzothiophene.…”

C–H and N–H activation by Pt(0) in N- and O-heteroaromatic compounds

“…Activation of the relatively weaker N-H bonds occurs more readily than at C-S or C-H bonds. In thiophene-like molecules, the Pt(PEt 3 ) 2 fragment inserts into the C(vinyl)-S bonds [3], although C-H activation can also occur in certain cases [6]. Oxygen-containing heteroaromatic compounds reacted via C-H activation at the a-carbon atoms, as was found for furan, benzoxazole and benzothiazole.…”

“…The insertion of a platinum(0) fragment into the strong C-O bond of benzofuran has been achieved by Sweigart and co-workers [5] when the benzofuran is activated by coordination of a Mn(CO) þ 3 group to benzofuranÕs carbocyclic ring. While studying C-S activations of platinum(0) with thiophenic substrates such as 2,2 0 -bithiophene and 2-(2-thienyl)-1-methylpyrrole, we found C-H activation to be a competing process (Scheme 1); C-S activation produced thiaplatinacycles, while C-H activation led to the formation of trans bisphosphine platinum(II) hydrides [6].…”

“…We thus became interested in extending our studies of platinum(0) oxidative addition reactions of thiophenes [6] to include other aromatic pexcessive heterocycles, such as furan and related molecules, to see if analogous reactions occur. As only a few examples of N-H activation of aromatic heterocycles have been reported for platinum(0) [10,11], we also wanted to do a more comprehensive and systematic study of N-H activation in pyrrole-like molecules.…”

Tunable charge-transport polarity in thienothiophene–bisoxoindolinylidene-benzodifurandione copolymers for high-performance field-effect transistors

“…]thiophene were prepared following the described procedures in literatures. 16,25,40,41 All air-and water-sensitive reactions were performed under argon atmosphere.…”