Kelvin L Billingsley

Massachusetts Institute of Technology, Cambridge, Massachusetts, United States

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Publications (9)59.93 Total impact

  • Alexander Duefert, Kelvin L Billingsley, Stephen L Buchwald
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    ABSTRACT: The Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles using precatalysts P1 or P2 is reported. The procedure allows for the reaction of variously substituted indazole, benzimidazole, pyrazole, indole, oxindole and azaindole halides under mild conditions in good to excellent yields. Additionally, the mechanism behind the inhibitory effect of unprotected azoles on Pd-catalyzed cross-coupling reactions is described based on evidence gained through experimental, crystallographic, and theoretical investigations.
    Journal of the American Chemical Society 08/2013; · 10.68 Impact Factor
  • Kelvin L. Billingsley, Stephen L. Buchwald
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    ABSTRACT: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
    ChemInform 10/2008; 39(41).
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    Kelvin L Billingsley, Stephen L Buchwald
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    ABSTRACT: A highly efficient method for the palladium-catalyzed borylation of aryl halides with an inexpensive and atom-economical boron source, pinacol borane, has been developed. This system allows for the conversion of aryl and heteroaryl iodides, bromides, and several chlorides, containing a variety of functional groups, to the corresponding pinacol boronate esters. In addition to the increase in substrate scope, this is the first general method where relatively low quantities of catalyst and short reaction times can be employed.
    The Journal of Organic Chemistry 08/2008; 73(14):5589-91. · 4.56 Impact Factor
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    Kelvin L Billingsley, Stephen L Buchwald
    Angewandte Chemie International Edition 02/2008; 47(25):4695-8. · 11.34 Impact Factor
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    Kelvin L Billingsley
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    ABSTRACT: Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008. Vita. Includes bibliographical references. Chapter 1. Highly active and efficient catalyst systems derived from palladium precatalysts and monophosphine ligands for the Suzuki-Miyaura cross-coupling reaction of heteroaryl boronic acids and esters has been developed. This method allows for the preparation of a wide variety of heterobiaryls in good to excellent yields and displays a high level of activity for the coupling of heteroaryl chlorides as well as hindered aryl and heteroaryl halides. Specific factors that govern the efficacy of the transformation for certain heterocyclic motifs were also investigated. Chapter 2. A highly efficient method for the palladium-catalyzed Suzuki-Miyaura reaction of lithium triisopropyl 2-pyridylborates has been developed. Catalysts comprised of Pd2dba3 and either diaryl or dialkyl phosphine oxide supporting ligands were found to be ideal for the transformation. This report represents one of the most general systems for the cross-coupling of aryl and heteroaryl bromides and chlorides with 2-pyridyl-derived nucleophiles. Chapter 3. Catalysts comprised of Pd and dialkylmonophosphinobiaryl ligands provide highly active systems for the borylation of aryl and heteroaryl chlorides. The direct preparation of symmetrical and unsymmetrical biaryls from two aryl chlorides without the need to isolate the intermediate boronate esters is also described. Additionally, computational studies provide insight into the roles of the biaryl phosphine ligand as well as KOAc in the catalytic cycle. Chapter 4. A highly efficient method for the palladium-catalyzed borylation of aryl halides with an inexpensive and atom-economical boron source, pinacol borane, has been developed. (cont.) This system allows for the conversion of aryl and heteroaryl iodides, bromides and several chlorides, containing a variety of functional groups, to the corresponding pinacol boronate esters. In addition to the increase in substrate scope, this is the first general method where relatively low quantities of catalyst and short reaction times can be employed. by Kelvin L. Billingsley. Ph.D.
    01/2008;
  • Kelvin L. Billingsley, Stephen L. Buchwald
    [Show abstract] [Hide abstract]
    ABSTRACT: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
    ChemInform 01/2008; 39(49).
  • Kelvin Billingsley, Stephen L Buchwald
    [Show abstract] [Hide abstract]
    ABSTRACT: A highly active and efficient catalyst system derived from a palladium precatalyst and monophosphine ligands 1 or 2 for the Suzuki-Miyaura cross-coupling reaction of heteroaryl boronic acids and esters has been developed. This method allows for the preparation of a wide variety of heterobiaryls in good to excellent yields and displays a high level of activity for the coupling of heteroaryl chlorides as well as hindered aryl and heteroaryl halides. Specific factors that govern the efficacy of the transformation for certain heterocyclic motifs were also investigated.
    Journal of the American Chemical Society 04/2007; 129(11):3358-66. · 10.68 Impact Factor
  • Kelvin L Billingsley, Timothy E Barder, Stephen L Buchwald
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    ABSTRACT: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
    Angewandte Chemie International Edition 02/2007; 46(28):5359-63. · 11.34 Impact Factor
  • Kelvin L Billingsley, Kevin W Anderson, Stephen L Buchwald
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    ABSTRACT: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
    Angewandte Chemie International Edition 06/2006; 45(21):3484-8. · 11.34 Impact Factor