Copper‐Catalyzed Direct Alkenylation of <i>N</i>‐Iminopyridinium Ylides

Mousseau, James J.; Bull, James A.; Charette, André B.

doi:10.1002/anie.200906020

Cited by 152 publications

(63 citation statements)

References 40 publications

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“…In 2009 Charette's group pursued investigations into the C–H alkenylation of N ‐benzoyliminopyridinium ylides such as 21 (Scheme ) with alkenyl iodides and found that treatment of 21 in the presence of K 2 CO 3 and a catalytic amount of CuBr 2 provided the C‐2 alkenylated derivatives 22 in moderate to good yields 35. This protocol constitutes the first ligand‐free Cu‐catalyzed direct alkenylation of electron‐deficient heteroarenes.…”

Section: Direct Intermolecular Alkenylationmentioning

confidence: 99%

Highly Modular POP Ligands for Asymmetric Hydrogenation: Synthesis, Catalytic Activity, and Mechanism

Fernández‐Pérez

Donald

Munslow

et al. 2010

Chemistry A European J

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A library of enantiomerically pure P-OP ligands (phosphine-phosphite), straightforwardly available in two synthetic steps from enantiopure Sharpless epoxy ethers is reported. Both the alkyloxy and phosphite groups can be optimized for maximum enantioselectivity and catalytic activity. Their excellent performance in the Rh-catalyzed asymmetric hydrogenation of a wide variety of functionalized alkenes (26 examples) and modular design makes them attractive for future applications. The lead catalyst incorporates an (S)-BINOL-derived (BINOL = 1,1'-bi-2-naphthol) phosphite group with computational studies revealing that this moiety has a dual effect on the behavior of our P-OP ligands. On one hand, the electronic properties of phosphite hinder the binding and reaction of the substrate in two out of the four possible manifolds. On the other hand, the steric effects of the BINOL allow for discrimination between the two remaining manifolds, thereby elucidating the high efficiency of these catalysts.

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Section: Direct Intermolecular Alkenylationmentioning

confidence: 99%

Highly Modular POP Ligands for Asymmetric Hydrogenation: Synthesis, Catalytic Activity, and Mechanism

Fernández‐Pérez

Donald

Munslow

et al. 2010

Chemistry A European J

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“…[4] In 2008, Doucet et al [5] successfully accomplished the palladiumcatalyzed direct C-H bond activation of benzoxazole and benzothiazole [2] with alkenyl bromides. More recently, other groups demonstrated that the palladium-catalyzed direct C-H alkenylation of imidazopyridines, [6] sydnones, [7] and N-iminopyridinium ylides [8] can be successfully achieved. Although these processes can compensate for the conventional coupling processes, they still suffer from some de-introduction of various mono-, di-, or trisubstituted alkenyl bromides as well as a benzyl chloride to the caffeine core.…”

Section: Introductionmentioning

confidence: 99%

Pd/Cu‐Catalyzed Direct Alkenylation of Azole Heterocycles with Alkenyl Halides

et al. 2010

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“…[16] Mechanistic studies suggested that the reaction went through a Cu(I)/CuA C H T U N G T R E N N U N G (III) catalytic cycle, and a copper exocyclic intermediate 26 was proposed. Wang and co-workers discovered the direct ortho-alkylation of N-iminopyridinium ylide 16 when N-tosylhydrazone 22 was employed as the substrate in the presence of CuI.…”

Section: à H Functionalization Of N-imide Ylidesmentioning

confidence: 99%

“…Asymmetric [3+2] cycloaddition of N-imide ylides. 16 asc.wiley-vch.de N-Iminoquinolinium ylide 198 was used as a substrate in the nickel-catalyzed cycloaddition of 1,1-cyclopropane diester 199, although a relatively poor diastereoselectivity was observed (Scheme 33). A nonconcerted mechanism combining nucleophilic ringopening of cyclopropane with subsequent nucleophilic addition was proposed.…”

Section: A C H T U N G T R E N N U N G [3+2] Cyclization Of N-imide Ymentioning

confidence: 99%

N‐Imide Ylide‐Based Reactions: CH Functionalization, Nucleophilic Addition and Cycloaddition

Qiu

Kuang

2014

Adv Synth Catal

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As valuable building blocks for introducing nitrogen, N-imide ylides represent an important class of reactive species and are synthons for the synthesis of nitrogen-containing heterocycles that potentially have biological activities. During the past decades, tremendous efforts have been devoted to the tandem processes involving N-imide ylides as well as their asymmetric applications. In particular, several types of N-imide ylide-based reactions have been established, such as C À H functionalization, nucleophilic addition, and cycloaddition, etc. In this review, recent advances in N-imide ylides chemistry are presented ordered according to the sequence of various reaction types.

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Copper‐Catalyzed Direct Alkenylation of N‐Iminopyridinium Ylides

Cited by 152 publications

References 40 publications

Highly Modular POP Ligands for Asymmetric Hydrogenation: Synthesis, Catalytic Activity, and Mechanism

Highly Modular POP Ligands for Asymmetric Hydrogenation: Synthesis, Catalytic Activity, and Mechanism

Pd/Cu‐Catalyzed Direct Alkenylation of Azole Heterocycles with Alkenyl Halides

N‐Imide Ylide‐Based Reactions: CH Functionalization, Nucleophilic Addition and Cycloaddition

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