111771-08-5Relevant academic research and scientific papers
Base- and Additive-Free Ir-Catalyzed ortho-Iodination of Benzoic Acids: Scope and Mechanistic Investigations
Erbing, Elis,Sanz-Marco, Amparo,Vázquez-Romero, Ana,Malmberg, Jesper,Johansson, Magnus J.,Gómez-Bengoa, Enrique,Martín-Matute, Belén
, p. 920 - 925 (2018/02/14)
A protocol for the C-H activation/iodination of benzoic acids catalyzed by a simple iridium complex has been developed. The method described in this paper allows the ortho-selective iodination of a variety of benzoic acids under extraordinarily mild conditions in the absence of any additive or base in 1,1,1,3,3,3-hexafluoroisopropanol as the solvent. The iridium catalyst used tolerates air and moisture, and selectively gives ortho-iodobenzoic acids with high conversions. Mechanistic investigations revealed that an Ir(III)/Ir(V) catalytic cycle operates, and that the unique properties of HFIP enables the C-H iodination using the carboxylic moiety as a directing group.
INHIBITORS OF STEAROYL-COA DESATURASE
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, (2009/06/27)
Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, obesity.
ISOQUINOLINES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS
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, (2008/12/08)
Disclosed herein are new isoquinoline compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibition of nitric oxide synthase activity in a human or animal subject are also provided for the treatment disease.
PdII-catalyzed monoselective ortho halogenation of C-H bonds assisted by counter cations: A complementary method to directed ortho lithiation
Mei, Tian-Sheng,Giri, Ramesh,Maugel, Nathan,Yu, Jin-Quan
supporting information; experimental part, p. 5215 - 5219 (2009/04/11)
(Chemical Equation Presented) When the counterion counts: The yield and selectivity of the title transformation of benzoic acid derivatives were improved greatly by using tetraalkyl ammonium salts as additives (see scheme; monoselectivity: 5:1-18:1). These effects are attributed to the influence of counter cations. The halogenated products are versatile intermediates for the construction of substituted aromatic compounds. DMF=N,N-dimethylformamide.
Promoting or preventing haloaryllithium isomerizations: Differential basicities and solvent effects as the crucial variables
Heiss, Christophe,Rausis, Thierry,Schlosser, Manfred
, p. 617 - 621 (2007/10/03)
Deprotonation-triggered heavy halogen migrations should become a favorite tool in arene synthesis if their occurrence and outcome could be made predictable. Particularly attractive, though extremely rare, are stop-and-go situations where a first intermediate, generated by metalation, can be trapped at -100 °C, whereas at -75 °C halogen migration gives rise to an isomer. As shown now, one can conveniently produce the initial aryllithium species by halogen/metal interconversion in toluene at -100 °C, under conditions that preclude, halogen migration, and unleash the isomerization process by adding tetrahydrofuran at -75 °C.
The basicity gradient-driven migration of iodine: Conferring regioflexibility on the substitution of fluoroarenes
Rausis, Thierry,Schlosser, Manfred
, p. 3351 - 3358 (2007/10/03)
Six different fluoroarenes were submitted to the same transformations. Direct deprotonation with alkyllithium or lithium dialkylamide as reagents and subsequent carboxylation afforded the acids 1, 6, 11, 16, 18, and 23. If the aryllithium intermediate was trapped with iodine rather than with dry ice, an iodofluoroarene (2, 7, 12, 17, 19, and 24) was formed. This, upon treatment with lithium diisopropylamide, underwent deprotonation and iodine migration. The resulting new aryllithium species was intercepted either by carboxylation, to give the acids 3, 8, 13, 20, and 25, or by neutralization, to produce the iodofluoroarenes 4, 9, 14, 21, and 26. The latter family of compounds was converted into another set of acids 5, 10, 15, 22, and 27 by subsequent treatment with butyllithium or isopropylmagnesium chloride and carbon dioxide. ( Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).
