Sequential N-Arylation of Primary Amines as a Route To Alkyldiarylamines

Harris, Michele C.; Geis, Oliver; Buchwald, Stephen L.

doi:10.1021/jo990568u

Cited by 99 publications

(38 citation statements)

References 14 publications

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“…As described in Scheme 2, the coupling reaction underwent a dramatic reversal of selectivity when the bulky biaryl phosphane ligand 4 developed by Buchwald and co-workers was used. [22] While the overall yield of the reaction was still high, the major product isolated from the reaction was the (Z)-substituted diene in a ratio of 74:26. This effect is not Table 2.…”

Section: Resultsmentioning

confidence: 99%

Construction of Highly Substituted Stereodefined Dienes by Cross‐Coupling of α‐Allenic Acetates

2006

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The assembly of highly substituted dienes remains a challenge for organic chemistry. This work represents a strategy for the construction of highly substituted 1,3-dienes by means of a Tsuji-Trost cross coupling between α-allenic acetates and organozinc reagents. The reaction is high yielding, and installs a trisubstituted olefin with E/Z selectivities up to 95:5 favoring the (E) product. A cheap, commercially available palladium precatalyst and a ligand are used to control the E/Z selectivity. Furthermore, an interesting reversal in selec-

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Section: Resultsmentioning

confidence: 99%

Construction of Highly Substituted Stereodefined Dienes by Cross‐Coupling of α‐Allenic Acetates

2006

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“…(41) and (42), by sequentially reacting aniline with two different aryl halides, or by reacting 4,4 0 -dibromobiphenyl with an arylamine and then a second aryl halide with DPPF-ligated palladium as the catalyst [250]. Buchwald subsequently published similar results on the formation of mixed alkyl diarylamines starting from a primary alkylamine [251] or a primary arylamine [252]. With ligand 15, good yields were obtained in one-pot syntheses of triarylamines.…”

Section: Synthesis Of Small Molecules For Materials Applicationsmentioning

confidence: 98%

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

Hartwig

2002

Modern Arene Chemistry

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The transition metal catalyzed synthesis of arylamines by the reaction of aryl halides or triflates with primary or secondary amines has become a valuable synthetic tool for many applications. This process forms monoalkyl or dialkyl anilines, mixed diarylamines or mixed triarylamines, as well as N-arylimines, carbamates, hydrazones, amides, and tosylamides. The mechanism of the process involves several new organometallic reactions. For example, the CaN bond is formed by reductive elimination of amine, and the metal amido complexes that undergo reductive elimination are formed in the catalytic cycle in some cases by NaH activation. Side products are formed by b-hydrogen elimination from amides, examples of which have recently been observed directly. An overview that covers the development of synthetic methods to form arylamines by this palladium-catalyzed chemistry is presented. In addition to the synthetic information, a description of the pertinent mechanistic data on the overall catalytic cycle, on each elementary reaction that comprises the catalytic cycle, and on competing side reactions is presented. The review covers manuscripts that appeared in press before June 1, 2001. This chapter is based on a review covering the literature up to September 1, 1999. However, roughly one-hundred papers on this topic have appeared since that time, requiring an updated review.

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“…[34] Es waren bereits zahlreiche Methoden zur Herstellung von Aporphinalkaloiden bekannt, aber die Bildung der entscheidenden Aryl-Aryl-Bindung war hinsichtlich der Effizienz (Ausbeute und Katalysatormenge) weiterhin von großer Bedeutung. Schließlich führte eine intramolekulare, Pd(OAc) 2 -katalysierte C-H-Kupplung von Bromarenen in Gegenwart von PhDavePhos 30 [35] und KOAc mit 99 % Ausbeute zu 31. Diese wichtige Zwischenverbindung wurde anschließend nach bekannten Verfahren in 32 und 33 überführt.…”

Section: C-c-bindungsbildung Durchunclassified

Funktionalisierung von C‐H‐Bindungen: neue Synthesemethoden für Naturstoffe und Pharmazeutika

2012

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Die direkte Funktionalisierung von C‐H‐Bindungen in organischen Molekülen hat sich in jüngster Zeit zu einer wirksamen und idealen Methode entwickelt, mit der Kohlenstoff‐Kohlenstoff‐ und Kohlenstoff‐Heteroatom‐Bindungen geknüpft werden können. Der Aufsatz gibt einen Überblick über die Strategien, die durch Funktionalisierung von C‐H‐Bindungen eine rasche Synthese von biologisch aktiven Verbindungen wie Naturstoffen und pharmazeutischen Zielsubstanzen ermöglichen.

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Sequential N-Arylation of Primary Amines as a Route To Alkyldiarylamines

Cited by 99 publications

References 14 publications

Construction of Highly Substituted Stereodefined Dienes by Cross‐Coupling of α‐Allenic Acetates

Construction of Highly Substituted Stereodefined Dienes by Cross‐Coupling of α‐Allenic Acetates

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

Funktionalisierung von C‐H‐Bindungen: neue Synthesemethoden für Naturstoffe und Pharmazeutika

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