Substrate-Directable Heck Reactions with Arenediazonium Salts. The Regio- and Stereoselective Arylation of Allylamine Derivatives and Applications in the Synthesis of Naftifine and Abamines

Prediger, Patrícia; Barbosa, Lais Ferreira; Génisson, Yves; Correia, Carlos Roque Duarte

doi:10.1021/jo201105z

Cited by 80 publications

(52 citation statements)

References 45 publications

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“…It is believed that the strong coordination of the nitrogen atom of allylic amine 2m to Pd could cause catalyst poisoning, thereby inhibiting the arylation. Similar poor performance of N , N ‐dialkylallylic amines has been reported recently 4b,5k,10b,c. It appears that the presence of a carbamate group in allylic amine substrates is necessary for high catalytic activity.…”

Section: Resultssupporting

confidence: 77%

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Palladium‐Catalyzed Regioselective and Stereoselective Oxidative Heck Arylation of Allylamines with Arylboronic Acids

Zhang¹,

Dong²,

Ding³

et al. 2013

Adv Synth Catal

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A general and convenient palladium-catalyzed oxidative Heck arylation of both N-protected and N,N-diprotected allylic amines with arylboronic acids under mild conditions has been developed. The catalyst system, consisting of PdA C H T U N G T R E N N U N G (OAc) 2 (palladium acetate), AgOAc (silver acetate) and KHF 2 (potassium hydrogen fluoride), could efficiently catalyze the coupling reaction in acetone without the aid of any ligand, leading exclusively to the g-arylated allylic amine products in good to excellent yields. This method is highlighted with excellent regio-and stereocontrol and remarkable functional group tolerance. The carbamate moiety in allylic amine substrates is of crucial importance to the catalytic performance, and the chelation between the carbonyl O (oxygen) and Pd (palladium) atoms is believed to be responsible for the high regioselectivity and stereoselectivity observed.

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Section: Resultssupporting

confidence: 77%

“…Finally, oxidation of the Pd(0) species by AgOAc regenerates the Pd(II) to complete the catalytic cycle. Similar chelation‐assisted regio‐ and stereocontrol has also been reported in the arylation of allyl derivatives and vinyl derivatives 4b,5k,7g,j,8e,f,13,14…”

Section: Resultssupporting

confidence: 65%

Palladium‐Catalyzed Regioselective and Stereoselective Oxidative Heck Arylation of Allylamines with Arylboronic Acids

Zhang¹,

Dong²,

Ding³

et al. 2013

Adv Synth Catal

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“…23). Correia 等 [33] 利用底物导向的 Heck 与芳基重氮盐的反应, 完成了区域和立体选择性的烯丙胺衍生物的芳基化并应用于 Naftifine 和 Abamines 的合成中(Scheme 8).…”

Section: Hiyama 交叉偶联反应unclassified

Research Progress on Cross-Coupling with Aryl Diazonium Salts

Xuan¹,

Wang²,

Wang³

et al. 2014

Chin. J. Org. Chem.

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Aryl diazonium salts have been widely used in cross-coupling reaction due to its easily available and highly reactivity as arylation reagents, which have drawn more and more attention by chemists in organic synthesis in recent years. The research progress since 2006 on cross-coupling with aryl diazonium salts combined with our work is reviewed, focusing on new applications and new progress of aryl diazonium salts in new method to build carbon-carbon bond, with construction of the natural product skeleton, in the field of heterogeneous catalysis and other aspects of green synthesis.

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“…[11][12][13][14] Inspired by the seminal review of Evans et al, we described these reactions as the Substrate-Directed Heck-Matsuda Reaction. This fact led us to realize that we could modulate and control the reactivity of the palladium species by substrates possessing chelating groups such as the carbonyl groups.…”

Section: Strategies and Tactics In Organic Synthesismentioning

confidence: 99%