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      Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: efficient synthesis of 1,1-diaryl-2,2-difluoroethenes

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          Summary

          The cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate ( 2) with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc) 2 and Na 2CO 3 afforded the mono-coupled products 3 and 5 in high yields. The use of 4 equiv of boronic acids in the presence of catalytic amount of Pd(PPh 3) 2Cl 2 and Na 2CO 3 in this reaction resulted in the formation of symmetrical di-coupled products 4 in high yields. Unsymmetrical di-coupled products 4 were obtained in high yields from the reactions of 3 with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc) 2 and Na 2CO 3.

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          Difluoromethyl 2-pyridyl sulfone: a new gem-difluoroolefination reagent for aldehydes and ketones.

          Difluoromethyl 2-pyridyl sulfone, a previously unknown compound, was found to act as a novel and efficient gem-difluoroolefination reagent for both aldehydes and ketones. It was found that the fluorinated sulfinate intermediate in the reaction is relatively stable, which can be observed by (19)F NMR and trapped with CH(3)I.
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            SSR182289A, a selective and potent orally active thrombin inhibitor.

            SSR182289A 1 is the result of a rational optimisation process leading to an orally active thrombin inhibitor. The structure incorporates an original 2-(acetylamino)-[1,1'-biphenyl]-3-sulfonyl N-terminal motif, a central l-Arg surrogate carrying a weakly basic 3-amino-pyridine, and an unusual 4-difluoropiperidine at the C-terminus. Its synthesis is convergent and palladium catalysis has been employed for the construction of the key C-C bonds: Suzuki coupling for the bis-aryl fragment and Sonogashira reaction for the delta- bond of the central amino-acid chain. The compound is a potent inhibitor of thrombin's activities in vitro and demonstrates potent oral anti-thrombotic potencies in three rat models of thrombosis. The observed in vitro potency could be rationalized through the examination of the interactions within the SSR182289A 1 - thrombin crystal structure. SSR182289A 1, has been therefore selected for further development.
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              Synthesis and biological activity of 5-(2,2-difluorovinyl)-2'-deoxyuridine

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                Author and article information

                Contributors
                Role: Guest Editor
                Journal
                Beilstein J Org Chem
                Beilstein J Org Chem
                Beilstein Journal of Organic Chemistry
                Beilstein-Institut (Trakehner Str. 7-9, 60487 Frankfurt am Main, Germany )
                1860-5397
                2013
                14 November 2013
                : 9
                : 2470-2475
                Affiliations
                [1 ]Department of Chemistry & Medical Chemistry, Yonsei University, 1 Yonseidae-gil, Wonju, Gangwondo 220-710, Republic of Korea
                Article
                10.3762/bjoc.9.286
                3869221
                24367415
                9d079f6e-20d1-42c2-9b36-819eb3cd5f4a
                Copyright © 2013, Kim et al; licensee Beilstein-Institut.

                This is an Open Access article under the terms of the Creative Commons Attribution License ( http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

                The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: ( http://www.beilstein-journals.org/bjoc)

                History
                : 27 August 2013
                : 22 October 2013
                Categories
                Full Research Paper
                Chemistry
                Organic Chemistry

                Organic & Biomolecular chemistry
                boronic acids,cross-coupling reaction,1,1-diaryl-2,2-difluoroethene,1,1-difluoro-1,3-dienes,2,2-difluoro-1-iodoethenyl tosylate,organo-fluorine

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