Iodination of aryltrimethylsilanes. A mild approach to (iodophenyl)alanine

Abstract

Supplementary Material Available: Crystallographic data including tables of the atomic positional and thermal parameters and bond angles for 10 (4 pages). Ordering information is given on any current masthead page.

Poly(2,7‐carbazole) Derivatives as Semiconductors for Organic Thin‐Film Transistors

“…Compound 2 was obtained from 3,5-dibromo-1-trimethylsilylbenzene and fresh octyl boronic acid through a special Suzuki coupling developed by Buchwald and coworkers [19] then subsequently converted to compound 3 using silver salt and iodine. [20] Finally, monomer 5 was obtained from 2,7-dibromo-9-H-carbazole [21] using a modern Ullmann arylation developed by Ma and coworkers. [22] The partial conversion of bromide function of compound 5 to the corresponding iodide function through Finkelstein reaction explains the modest yield obtained as previously observed for other similar reactions.…”

Regioselective iodination of chlorinated aromatic compounds using silver salts

“…38 Although AgBF 4 /I 2 has been used for the synthesis of iodoarenes from aryltrimethylsilanes, this reagent has not been investigated for the direct electrophilic iodination of aromatic compounds. 39,40 Furthermore, several other iodinating reagents, such as bis(sym-collidine)iodine(I) hexafluorophosphate 41 or HgO/HBF 4 /I 2 on SiO 3 , 42 contain non-coordinating anions. However, to the best of our knowledge iodination reactions with I 2 and AgSbF 6 , AgBF 4 or AgPF 6 have not been employed in aromatic iodination reactions.…”

Anodic Cyanation of Arylsilanes without Elimination of Silyl Groups

“…High-resolution mass spectrum, Calcd. for C 16 Detrimethylsilylation of 6a: A mixture of 6a (5 mmol) and 30 mL of trifluoroacetic acid was heated at 5055°C for 15 h. The reaction mixture was poured into a saturated sodium bicarbonate solution; the products were extracted with ether and were purified by distillation. The ratio of isomers 3a and 3b was determined by NMR.…”

“…12,13 In contrast, general chemical reactions of arylsilanes, vinylsilanes and allylsilanes usually accompany with the cleavage of the carbonsilicon bond. 14,15 The carbon-silicon bond cannot be cleaved by any nucleophile, such as the cyanide anion, although electrophiles such as I + , Br + , Cl + , 16 acyl, 17 and NO 2 + , 18 can readily cleave it. Furthermore, the electrochemical oxidation of vinylsilanes and allylsilanes has also been reported to yield desilylated compounds; 14 therefore, the electrochemical introduction of a functional group in the vinylic and allylic moiety also accompanies with desilylation.…”