18312-48-6Relevant articles and documents
Facile and direct synthesis of symmetrical acid anhydrides using a newly prepared powerful and efficient mixed reagent
Rouhi-Saadabad, Hamed,Akhlaghinia, Batool
, p. 479 - 485 (2015/01/30)
An efficient mixed reagent for direct synthesis of symmetrical carboxylic anhydrides from carboxylic acids has been prepared. Carboxylic acids are converted to anhydrides using triphenylphosphine/ trichloroisocyanuric acid under mild reaction conditions at room temperature. Short reaction time, excellent yields of products, low cost, availability of reagents, simple experimental procedure, and easy work-up of the products are the main advantages of the presented method.
Decarboxylative cross-coupling of mesylates catalyzed by copper/palladium systems with customized imidazolyl phosphine ligands
Song, Bingrui,Knauber, Thomas,Goo?en, Lukas J.
supporting information, p. 2954 - 2958 (2013/04/11)
The activation of the inert C-O bonds in mesylates through the use of a new class of imidazolyl phosphines allows the decarboxylative coupling of aryl mesylates as well as polysubstituted alkenyl mesylates. Variation of the ligands leads to two complementary methods providing the corresponding biaryls and polysubstituted olefins in good yields. Copyright
Decarboxylative cross-coupling of aryl tosylates with aromatic carboxylate salts
Goossen, Luksa J.,Rodriguez, Nuria,Lange, Paul P.,Linder, Christophe
supporting information; experimental part, p. 1111 - 1114 (2010/04/29)
(Figure Presented) A bimetallic copper/palladium catalyst system is disclosed that enables the use of tosylates as carbon electrophiles in decarboxylative coupling reactions. A variety of aromatic carboxylate salts, regardless of their substitution pattern, have been coupled with these inexpensive and readily available electrophiles to give the corresponding biaryl compounds in good yields (see scheme).
Pd-catalyzed decarboxylative Heck vinylation of 2-nitrobenzoates in the presence of CuF2
Goossen, Lukas J.,Zimmermann, Bettina,Knauber, Thomas
supporting information; experimental part, (2010/08/19)
A new protocol for the decarboxylative Heck vinylation of benzoic acids is disclosed. In the presence of a catalyst system generated in situ from Pd(OAc)2 (2 mol %), CuF2 (2 equiv), and benzoquinone (0.5 equiv) in NMP, a wide range of olefins were coupled with various 2-nitrobenzoates at 130 °C with the release of carbon dioxide to afford the corresponding vinyl arenes in good yields.
Biaryl and aryl ketone synthesis via Pd-catalyzed decarboxylase coupling of carboxylate salts with aryl triflates
Goossen, Lukas J.,Linder, Christophe,Rodriguez, Nuria,Lange, Paul P.
supporting information; experimental part, p. 9336 - 9349 (2010/04/03)
A bimetallic catalyst system has been developed that for the first time allows the decarboxylative crosscoupling of aryl and acyl carboxylates with aryl triflates. In contrast to aryl halides, these electrophiles give rise to non-coordinating anions as byproducts, which do not interfere with the decarboxylation step that leads to the generation of the carbon nucleophilic crosscoupling partner. As a result, the scope of carboxylate substrates usable in this transformation was extended from ortho-substituted or otherwise activated derivatives to a broad range of ortho-, meta-, and para-substituted aromatic carboxylates. Two alternative protocols have been optimized, one involving heating the substrates in the presence of CuI/1,10- phenanthroline (10-15 mol %) and PdI2/phosphine (23 mol%) in NMP for 1-24 h, the other involving CuI/l,10-phenanthroline (615mol%) and PdBr2/Tol-BINAP (2 mol % ) in NMP using microwave heating for 5-10 min. While most products are accessible using standard heating, the use of microwave irradiation was found to be beneficial especially for the conversion of non-activated carboxylates with functionalized aryl triflates. The synthetic utility of the transformation is demonstrated with 48 examples showing the scope and limitations of both protocols. In mechanistic studies, the special role of microwave irradiation is elucidated, and further perspectives of decarboxylase crosscouplings are discussed.
Synthesis of biaryls and aryl ketones via microwave-assisted decarboxylative cross-couplings
Goossen, Lukas J.,Linder, Bettina Zimmermanns Christophe,Rodriguez, Nuria,Lange, Paul P.,Hartung, Jens
experimental part, p. 2667 - 2674 (2009/12/31)
A protocol for the microwave-assisted decarboxylative cross-couplings of carboxylic acid salts with aryl halides has been developed that allows the synthesis of various biaryls and aryl ketones in high yields. After careful adaptation of the bimetallic ca
Decarboxylative biaryl synthesis from aromatic carboxylates and aryl triflates
Goossen, Lukas J.,Rodriguez, Nuria,Linder, Christophe
supporting information; experimental part, p. 15248 - 15249 (2009/03/11)
A new catalyst system, generated in situ from Cu2O, 1,10-phenanthroline, PdI2, and Tol-BINAP, for the first time allows the decarboxylative coupling of carboxylic acids with aryl triflates. In contrast to previous decarboxylative couplings that remained limited to certain activated carboxylates, e.g., ortho-substituted benzoates, this halide-free protocol is generally applicable to aromatic carboxylic acid salts regardless of their substitution pattern. Copyright
