Direct Arylation as a Synthetic Tool for the Synthesis of Thiophene-Based Organic Electronic Materials

Thiophene-Fused Tropones as Chemical Warfare Agent-Responsive Building Blocks

“…We ultimately found the previously reported conditions 30,31 of Pd(OAc) 2 , PCy 3 ·HBF 4 , pivalic acid, and K 2 CO 3 in dimethylacetamide at 100°C for 12 hours to be the optimized reaction conditions. Higher molecular weights were obtained, although polymers P1b (Mn=6.20 kDa, PDI=1.98) and P1c (Mn=7.60 kDa, PDI=2.61) remained only moderately soluble in organic solvents, despite the inclusion of two solubilizing 2-ethylhexyl chains in P1c.…”

Biaryl Synthesis through Metal‐Catalyzed C–H Arylation

“…When catalytic amounts of both Herrmann's palladium catalyst 74 and tris(N,N-dimethylaniline)phosphine (75) were used, 2-bromo-3-hexylthiophene was successfully converted into poly(3-hexylthiophene) with a high molecular weight (M n up to 30 600) and high regioregularity (up to 98%). In 2011, Schipper [94] reported the synthesis of potent organic electronics material through a palladium-catalyzed C-H arylation of thiophenes. For example, compound 76, a donor material in heterojunction solar cells [96], and compound 77, a fluorescent marker for in vivo optical imaging [97], can be rapidly synthesized by C-H/C-X coupling of the corresponding thiophenes and aryl halides without any prefunctionalization of the thiophene moieties.…”

Air‐Stable Manganese(I)‐Catalyzed C−H Activation for Decarboxylative C−H/C−O Cleavages in Water

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The decarboxylative C À H/C À Of unctionalization was accomplished by air-a nd water-tolerant manganese(I) catalysis.T he versatile CÀHa llylation occurred by facile organometallic CÀHm etalation on indoles,a renes,a mino acids and synthetically meaningful aryl ketimines with ample substrate scope and high levels of chemo-, site-and regioselectivity.CÀHf unctionalization technology has emerged as an increasingly powerful tool for molecular syntheses, [1] with enabling applications to material sciences, [2] crop protection [3] and drug development. [4] While significant advances have been achieved with the aid of precious 4d and 5d transition metal complexes, [5] recent focus has shifted towards the use of earth-abundant base metals.

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“…CÀHf unctionalization technology has emerged as an increasingly powerful tool for molecular syntheses, [1] with enabling applications to material sciences, [2] crop protection [3] and drug development. [4] While significant advances have been achieved with the aid of precious 4d and 5d transition metal complexes, [5] recent focus has shifted towards the use of earth-abundant base metals.…”