Synthesis of ene–allenes via palladium-catalyzed hydride-transfer reaction of propargylic amines under mild conditions

Nakamura, Hiroyuki; Tashiro, Satoshi; Kamakura, Takaya

doi:10.1016/j.tetlet.2005.09.169

Cited by 25 publications

(13 citation statements)

References 18 publications

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“…A palladium-catalyzed formation of a 1,3-diene from an allylic benzoate was used in a synthesis of tuberostemonines [688]. Palladium catalyzed the transformation of 1-aryl-3-N,N-dialkyl-1-propynes to 1-aryl-1,2-propadienes [306,689]. (94) Palladium-catalyzed coupling of allylic bromides with trimethylstannylphenylselenide to give allylic phenylselenides [22].…”

Section: Carbon-heteroatom Bond-forming Reactions Using Heteroatom Numentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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Section: Carbon-heteroatom Bond-forming Reactions Using Heteroatom Numentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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“…The synthesis of ene-allenes 115, 117, 119 in high yields from the corresponding propargylic amines 114, 116,118, respectively, at room temperature was recently reported by Nakamura et al [77], Scheme 16. The reaction proceeded in the presence of Pd 2 (dba) 3 -CHCl 3 (5 mol %) and (C 6 F 5 ) 2 PC 2 H 4 P(C 6 F 5 ) 2 (10 mol %) in CHCl 3 and different substituents on the nitrogen of propargylic amines including dicyclohexyl groups were found to be effective for the transformation.…”

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confidence: 85%

Recent Progress in the Chemistry of Allenes

Hassan

2007

COS

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Allenes are important compounds in organic and synthetic organic chemistry and therefore a large number of studies on their synthesis and reactions have been reported so far. We report the most recent methods for the synthesis of allenes, including optically active forms and fluorinated and gem-difluorinated allenes, in this paper. Reactions such as nucleophilic addition of allenes were classified and discussed in details according to the nature of the nucleophile either oxygen, nitrogen, carbon or sulfur, whereas, inter-and intra-molecular cycloadditions reactions with a variety of unsaturated functionality were separately discussed. A collection of some useful reactions such as coupling reactions of allenes mediated by organometallic reagents, intramolecular cyclization of allenes with tethered amines, asymmetric dihydroxylation, and epoxidation of allenes are also included.

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“…15 Reaction of the propargylic alcohols 1f-i and the acetate 1j also proceeded without affecting OH and OAc groups 8 to afford the corresponding allenyl carbinols 2f-i and allenyl acetate 2j in good to high yields (entries 6-10). The current transformation was able to be applied for aliphatic alkyne 1k, aromatic alkyne 1l, and biologically active alkynes 1m-n (entries [11][12][13][14]. 16,17 Bn2N NBn2…”

Section: (Mannich-type Product)mentioning

confidence: 99%

“…Although the reaction was complete within 5 min using a 30 mol % of CuBr, 2a was generated only in 45% for 1 min (entries 5-7). N,N-Dicyclohexylamine was more effective for this transformation 13 and 2a was obtained in 76% yield even for 1 min at [11][12][13]. Other cupper catalysts, such as CuCl, CuI, CuOAc, and CuCl 2 were not effective for this transformation (entries 14-17) and the reaction did not proceed under palladiumcatalyzed conditions (entries 18 and 19).…”

Section: Introductionmentioning

confidence: 99%