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  1. Article ; Online: A Noncoordinating Acid-Base Catalyst for the Mild and Nonreversible

    Fandrick, Keith R / Patel, Nitinchandra D / Radomkit, Suttipol / Chatterjee, Arindom / Braith, Stefan / Fandrick, Daniel R / Busacca, Carl A / Senanayake, Chris H

    The Journal of organic chemistry

    2021  Volume 86, Issue 6, Page(s) 4877–4882

    Abstract: A mild and ... ...

    Abstract A mild and nonreversible
    MeSH term(s) Acids ; Alcohols ; Catalysis ; Ethers ; Phenols
    Chemical Substances Acids ; Alcohols ; Ethers ; Phenols
    Language English
    Publishing date 2021-03-09
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.1c00193
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  2. Article: A Noncoordinating Acid–Base Catalyst for the Mild and Nonreversible tert-Butylation of Alcohols and Phenols

    Fandrick, Keith R. / Patel, Nitinchandra D. / Radomkit, Suttipol / Chatterjee, Arindom / Braith, Stefan / Fandrick, Daniel R. / Busacca, Carl A. / Senanayake, Chris H.

    Journal of organic chemistry. 2021 Mar. 09, v. 86, no. 6

    2021  

    Abstract: A mild and nonreversible tert-butylation of alcohols and phenols can be achieved in high yields using the noncoordinating acid–base catalyst [bis(trifluoromethane)sulfonimide and 2,6-lutidine] with a tert-butylation reagent, tert-butyl 2,2,2- ... ...

    Abstract A mild and nonreversible tert-butylation of alcohols and phenols can be achieved in high yields using the noncoordinating acid–base catalyst [bis(trifluoromethane)sulfonimide and 2,6-lutidine] with a tert-butylation reagent, tert-butyl 2,2,2-trichloroacetimidate. This method allows the use of substrates containing acid sensitive groups such as ketal, Boc, and boronate esters.
    Keywords acids ; catalysts ; esters ; journals ; methodology ; organic chemistry ; phenol
    Language English
    Dates of publication 2021-0309
    Size p. 4877-4882.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.1c00193
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  3. Article ; Online: Sulfone-Mediated S

    Patel, Nitinchandra D / Wei, Xudong / Byrne, Denis / Narayanan, Bikshandarkoil A / Pennino, Scott / Sarvestani, Max / Saha, Anjan / Haddad, Nizar / Kapadia, Suresh / Lorenz, Jon C / DeCroos, Philomen / Ye, Andrew / Lee, Heewon / Grinberg, Nelu / Hossain, Azad / Busacca, Carl A / Yee, Nathan K / Senanayake, Chris H

    The Journal of organic chemistry

    2020  Volume 85, Issue 13, Page(s) 8339–8351

    Abstract: An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive ... ...

    Abstract An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive S
    MeSH term(s) Antiviral Agents ; Ethers ; Hepacivirus ; Hepatitis C ; Humans ; Protease Inhibitors/pharmacology ; Sulfones ; Viral Nonstructural Proteins
    Chemical Substances Antiviral Agents ; Ethers ; Protease Inhibitors ; Sulfones ; Viral Nonstructural Proteins
    Language English
    Publishing date 2020-06-19
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.0c00554
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article: Sulfone-Mediated SNAr Reaction as a Powerful Tool for the Synthesis of 4-Quinolinyl Ethers and More—Application to the Synthesis of HCV NS3/4a Protease Inhibitor BI 201420

    Patel, Nitinchandra D. / Wei, Xudong / Byrne, Denis / Narayanan, Bikshandarkoil A. / Pennino, Scott / Sarvestani, Max / Saha, Anjan / Haddad, Nizar / Kapadia, Suresh / Lorenz, Jon C. / DeCroos, Philomen / Ye, Andrew / Lee, Heewon / Grinberg, Nelu / Hossain, Azad / Busacca, Carl A. / Yee, Nathan K. / Senanayake, Chris H.

    Journal of organic chemistry. 2020 May 28, v. 85, no. 13

    2020  

    Abstract: An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive SNAr reaction of 4-quinolinyl sulfones with a range of structurally diversified 1°, 2°, and 3° alcohols with a wide substrate scope and high ... ...

    Abstract An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive SNAr reaction of 4-quinolinyl sulfones with a range of structurally diversified 1°, 2°, and 3° alcohols with a wide substrate scope and high yields. By adapting this methodology, a convergent synthesis of a complex target of HCV NS3/4a protease inhibitor BI 201420 was accomplished.
    Keywords alcohols ; ethers ; journals ; organic chemistry ; proteinase inhibitors
    Language English
    Dates of publication 2020-0528
    Size p. 8339-8351.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.0c00554
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  5. Article ; Online: A Computational Investigation of the Ligand-Controlled Cu-Catalyzed Site-Selective Propargylation and Allenylation of Carbonyl Compounds.

    Zou, Yike / Gutierrez, Osvaldo / Sader, Avery C / Patel, Nitinchandra D / Fandrick, Daniel R / Busacca, Carl A / Fandrick, Keith R / Kozlowski, Marisa / Senanayake, Chris H

    Organic letters

    2017  Volume 19, Issue 22, Page(s) 6064–6067

    Abstract: A copper-catalyzed site-selective propargylation/allenylation reaction toward carbonyl compounds has been mechanistically investigated using a computational approach. Different reaction pathways and catalytic cycles were investigated. Control of the site ...

    Abstract A copper-catalyzed site-selective propargylation/allenylation reaction toward carbonyl compounds has been mechanistically investigated using a computational approach. Different reaction pathways and catalytic cycles were investigated. Control of the site selectivity arises from a destabilizing interaction introduced by the phenyl-substituted ligand.
    MeSH term(s) Alkadienes/chemistry ; Catalysis ; Copper ; Ketones ; Ligands ; Molecular Structure
    Chemical Substances Alkadienes ; Ketones ; Ligands ; propadiene (4AV0LZ8QKB) ; Copper (789U1901C5)
    Language English
    Publishing date 2017-11-02
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.7b02845
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article ; Online: One-pot synthesis of 2,5-disubstituted pyrimidines from nitriles.

    Frutos, Rogelio P / Wei, Xudong / Patel, Nitinchandra D / Tampone, Thomas G / Mulder, Jason A / Busacca, Carl A / Senanayake, Chris H

    The Journal of organic chemistry

    2013  Volume 78, Issue 11, Page(s) 5800–5803

    Abstract: A practical, one-step process for the synthesis of 2,5-disubstituted pyrimidines is presented. The protocol proved to be general for the synthesis of a variety of pyrimidine-containing compounds bearing an assortment of functional groups. ...

    Abstract A practical, one-step process for the synthesis of 2,5-disubstituted pyrimidines is presented. The protocol proved to be general for the synthesis of a variety of pyrimidine-containing compounds bearing an assortment of functional groups.
    MeSH term(s) Molecular Structure ; Nitriles/chemistry ; Pyrimidines/chemical synthesis ; Pyrimidines/chemistry
    Chemical Substances Nitriles ; Pyrimidines
    Language English
    Publishing date 2013-06-07
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/jo400720p
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  7. Article ; Online: Ligand-Accelerated Stereoretentive Suzuki-Miyaura Coupling of Unprotected 3,3'-Dibromo-BINOL.

    Qu, Bo / Haddad, Nizar / Rodriguez, Sonia / Sieber, Joshua D / Desrosiers, Jean-Nicolas / Patel, Nitinchandra D / Zhang, Yongda / Grinberg, Nelu / Lee, Heewon / Ma, Shengli / Ries, Uwe Jörg / Yee, Nathan K / Senanayake, Chris H

    The Journal of organic chemistry

    2016  Volume 81, Issue 3, Page(s) 745–750

    Abstract: An efficient synthesis of the enantiomerically pure 3,3'-bis-arylated BINOL derivatives is accomplished through the palladium-catalyzed Suzuki-Miyaura coupling of the unprotected 3,3'-dibromo-BINOL with complete retention of enantiopurity. The active ... ...

    Abstract An efficient synthesis of the enantiomerically pure 3,3'-bis-arylated BINOL derivatives is accomplished through the palladium-catalyzed Suzuki-Miyaura coupling of the unprotected 3,3'-dibromo-BINOL with complete retention of enantiopurity. The active catalyst system Pd(OAc)2/BI-DIME has enabled mild reaction conditions at palladium loads as low as 500 ppm.
    Language English
    Publishing date 2016-02-05
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.5b02368
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

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  8. Article: Ligand-Accelerated Stereoretentive Suzuki–Miyaura Coupling of Unprotected 3,3′-Dibromo-BINOL

    Qu, Bo / Haddad Nizar / Rodriguez Sonia / Sieber Joshua D / Desrosiers Jean-Nicolas / Patel Nitinchandra D / Zhang Yongda / Grinberg Nelu / Lee Heewon / Ma Shengli / Ries Uwe Jörg / Yee Nathan K / Senanayake Chris H

    Journal of organic chemistry. 2016 Feb. 05, v. 81, no. 3

    2016  

    Abstract: An efficient synthesis of the enantiomerically pure 3,3′-bis-arylated BINOL derivatives is accomplished through the palladium-catalyzed Suzuki–Miyaura coupling of the unprotected 3,3′-dibromo-BINOL with complete retention of enantiopurity. The ... ...

    Abstract An efficient synthesis of the enantiomerically pure 3,3′-bis-arylated BINOL derivatives is accomplished through the palladium-catalyzed Suzuki–Miyaura coupling of the unprotected 3,3′-dibromo-BINOL with complete retention of enantiopurity. The active catalyst system Pd(OAc)₂/BI-DIME has enabled mild reaction conditions at palladium loads as low as 500 ppm.
    Keywords Suzuki reaction ; catalysts ; catalytic activity ; chemical structure ; organic chemistry ; organic compounds ; palladium
    Language English
    Dates of publication 2016-0205
    Size p. 745-750.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021%2Facs.joc.5b02368
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  9. Article: One-Pot Synthesis of 2,5-Disubstituted Pyrimidines from Nitriles

    Frutos, Rogelio P / Wei Xudong / Patel Nitinchandra D / Tampone Thomas G / Mulder Jason A / Busacca Carl A / Senanayake Chris H

    Journal of organic chemistry. 2013 June 07, v. 78, no. 11

    2013  

    Abstract: A practical, one-step process for the synthesis of 2,5-disubstituted pyrimidines is presented. The protocol proved to be general for the synthesis of a variety of pyrimidine-containing compounds bearing an assortment of functional groups. ...

    Abstract A practical, one-step process for the synthesis of 2,5-disubstituted pyrimidines is presented. The protocol proved to be general for the synthesis of a variety of pyrimidine-containing compounds bearing an assortment of functional groups.
    Keywords chemical reactions ; moieties ; nitriles ; organic chemistry ; pyrimidines ; synthesis
    Language English
    Dates of publication 2013-0607
    Size p. 5800-5803.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021%2Fjo400720p
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  10. Article: Copper-Catalyst-Controlled Site-Selective Allenylation of Ketones and Aldehydes with Propargyl Boronates

    Fandrick, Keith R / Ogikubo Junichi / Fandrick Daniel R / Patel Nitinchandra D / Saha Jaideep / Lee Heewon / Ma Shengli / Grinberg Nelu / Busacca Carl A / Senanayake Chris H

    Organic letters. 2013 Mar. 15, v. 15, no. 6

    2013  

    Abstract: A practical and highly site-selective copper-PhBPE-catalyst-controlled allenylation with propargyl boronates has been developed. The methodology has shown to be tolerant of diverse ketones and aldehydes providing the allenyl adducts in high selectivity. ... ...

    Abstract A practical and highly site-selective copper-PhBPE-catalyst-controlled allenylation with propargyl boronates has been developed. The methodology has shown to be tolerant of diverse ketones and aldehydes providing the allenyl adducts in high selectivity. The BPE ligand and boronate substituents were shown to direct the site selectivity for which either propargyl or allenyl adducts can be acquired in high selectivity. A model is proposed that explains the origin of the site selectivity.
    Keywords aldehydes ; chemical reactions ; chemical structure ; ketones ; ligands ; models
    Language English
    Dates of publication 2013-0315
    Size p. 1214-1217.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1523-7052
    DOI 10.1021%2Fol400124f
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