939-37-7Relevant articles and documents
Stereoretentive Pd-catalysed Stille cross-coupling reactions of secondary alkyl azastannatranes and aryl halides
Li, Ling,Wang, Chao-Yuan,Huang, Rongcai,Biscoe, Mark R.
, p. 607 - 612 (2013/07/26)
The development of transition metal-catalysed cross-coupling reactions has greatly influenced the manner in which the synthesis of complex organic molecules is approached. A wide variety of methods are now available for the formation of C(sp2)-C(sp2) bonds, and more recent work has focused on the use of C(sp3) electrophiles and nucleophiles. The use of secondary and tertiary alkyl nucleophiles in cross-coupling reactions remains a challenge because of the propensity of these alkyl groups to isomerize under the reaction conditions. Here, we report the development of a general Pd-catalysed process for the stereoretentive cross-coupling of secondary alkyl azastannatrane nucleophiles with aryl chlorides, bromides, iodides and triflates. Coupling partners with a wide range of electronic characteristics are well tolerated. The reaction occurs with minimal isomerization of the secondary alkyltin nucleophile, and with retention of absolute configuration. This process constitutes the first general method to use secondary alkyltin reagents in cross-coupling reactions.
Process for the preparation of alkylated aromatic carboxylic acids and acyl halides
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, (2008/06/13)
The invention relates to a process for the preparation of polyalkylated aromatic carboxylic acids of formula I STR1 wherein R1, R2, R3, R4 and R5 are each independently of one another hydrogen, C1 -C20 alkyl, halogen or C5 -C8 cycloalkyl, with the proviso that at least two of the substituents R1, R2, R3, R4 or R5 are alkyl and/or cycloalkyl, by reacting corresponding aromatic hydrocarbons with carbon dioxide, which reaction is carried out observing special ratios of temperature and pressure. The invention furthermore relates to a one-pot process for the preparation of the corresponding acyl halides.