Siloxane-Based Cross-Coupling of Bromopyridine Derivatives: Studies for the Synthesis of Streptonigrin and Lavendamycin
Highly functionalized 4-bromopyridines were prepared and found to undergo fluoride-promoted, Pd-catalyzed cross-coupling with aryltrialkoxysilanes to give sterically demanding biaryls. The 3-nitro-4-bromopyridine derivative coupled in good yield with TBAT (tetrabutylammonium triphenyldifluorosilicat...
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Published in | Organic letters Vol. 5; no. 25; pp. 4779 - 4782 |
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Main Authors | , |
Format | Journal Article |
Language | English |
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WASHINGTON
American Chemical Society
11.12.2003
Amer Chemical Soc |
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Abstract | Highly functionalized 4-bromopyridines were prepared and found to undergo fluoride-promoted, Pd-catalyzed cross-coupling with aryltrialkoxysilanes to give sterically demanding biaryls. The 3-nitro-4-bromopyridine derivative coupled in good yield with TBAT (tetrabutylammonium triphenyldifluorosilicate) to provide a biaryl adduct that serves as a model system for the total synthesis of the antitumor antibiotics streptonigrin and lavendamycin. |
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AbstractList | Highly functionalized 4-bromopyridines were prepared and found to undergo fluoride-promoted, Pd-catalyzed cross-coupling with aryltrialkoxysilanes to give sterically demanding biaryls. The 3-nitro-4-bromopyridine derivative coupled in good yield with TBAT (tetrabutylammonium triphenyldifluorosilicate) to provide a biaryl adduct that serves as a model system for the total synthesis of the antitumor antibiotics streptonigrin and lavendamycin. Highly functionalized 4-bromopyridines were prepared and found to undergo fluoride-promoted, Pd-catalyzed cross-coupling with aryltrialkoxysilanes to give sterically demanding biaryls. The 3-nitro-4-bromopyridine derivative coupled in good yield with TBAT (tetrabutylammonium triphenyldifluorosilicate) to provide a biaryl adduct that serves as a model system for the total synthesis of the antitumor antibiotics streptonigrin and lavendamycin. [reaction: see text] [GRAPHICS] Highly functionalized 4-bromopyridines were prepared and found to undergo fluoride-promoted, Pd-catalyzed cross-coupling with aryltrialkoxysilanes to give sterically demanding biaryls. The 3-nitro-4-bromopyridine derivative coupled in good yield with TBAT (tetrabutylammonium triphenyidifluorosilicate) to provide a biaryl adduct that serves as a model system for the total synthesis of the antitumor antibiotics streptonigrin and lavendamycin. |
Author | DeShong, Philip McElroy, William T |
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Snippet | Highly functionalized 4-bromopyridines were prepared and found to undergo fluoride-promoted, Pd-catalyzed cross-coupling with aryltrialkoxysilanes to give... [GRAPHICS] Highly functionalized 4-bromopyridines were prepared and found to undergo fluoride-promoted, Pd-catalyzed cross-coupling with aryltrialkoxysilanes... |
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SubjectTerms | Antibiotics, Antineoplastic - chemical synthesis Chemistry Chemistry, Organic Molecular Structure Physical Sciences Pyridines - chemical synthesis Pyridines - chemistry Science & Technology Siloxanes - chemistry Streptonigrin - analogs & derivatives Streptonigrin - chemical synthesis |
Title | Siloxane-Based Cross-Coupling of Bromopyridine Derivatives: Studies for the Synthesis of Streptonigrin and Lavendamycin |
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