Zinc barbier reaction of propargyl halides in water

Bieber, Lothar W.; Silva, Margarete F. da; Costa, Rosenildo Corrêa da; Silva, Lília O.S.

doi:10.1016/s0040-4039(98)00641-8

Cited by 44 publications

(13 citation statements)

References 13 publications

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“…www.chemeurj.org commonly found in previously described propargylation methods. [11][12][13][14][15][16][17][18] Additionally, considerable stereoselectivity was observed for the propargylation of a-substituted aldehyde 7 (Table 1, entry 2; syn/anti = 9:1), which can be understood by Crams rule. [31] It should be noted that the reactions took place at room temperature under mild conditions compatible with several functional groups, including conjugated alkynes, esters, fluorides, chlorides, and bromides.…”

Section: Resultsmentioning

confidence: 99%

Highly Selective Barbier‐Type Propargylations and Allenylations Catalyzed by Titanocene(III)

Muñoz-Bascón

Sancho‐Sanz

Álvarez-Manzaneda

et al. 2012

Chemistry A European J

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The alkyne functional group is found in many bioactive natural products and is the key to many important chemical transformations developed over recent years. Moreover, allenes have recently gained relevance as versatile reagents in organic synthesis. Mild, catalytic methods to enable the selective introduction of either alkyne or allene motifs into organic molecules are very valuable but, as yet, quite scarce. We describe an extremely mild and selective method for either the propargylation or allenylation of carbonyl compounds catalyzed by the abundant, safe, and inexpensive metal titanium. These reactions can selectively provide homopropargylic alcohols from aldehydes and ketones or α-hydroxy-allenes from aldehydes. The mechanisms involved were also investigated.

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Section: Resultsmentioning

confidence: 99%

Highly Selective Barbier‐Type Propargylations and Allenylations Catalyzed by Titanocene(III)

Muñoz-Bascón

Sancho‐Sanz

Álvarez-Manzaneda

et al. 2012

Chemistry A European J

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“…A new compound, (I), was synthesized by an extension of the Reformatsky reaction (Bieber et al, 1997) in aqueous media (Chan et al, 1994;Shen et al, 1997). A new aqueous system (Bieber et al, 1998;Li, 1996) was designed in the reaction of a 2-bromoketone with an aromatic aldehyde and good results were obtained. It is the ®rst time that the reaction has been carried out in aqueous media in the presence of zinc.…”

Section: Commentmentioning

confidence: 99%

3-(2,4-Dichlorophenyl)-3-hydroxy-1-phenylpropan-1-one

et al. 2003

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“…Bieber and coworkers pioneered the studies of organometallic reactions with carbonyl compounds in water such as the propargylation of aldehydes in the presence of zinc powder in concentrated aqueous salt solutions in moderate to good yields (Bieber et al 1998).…”

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confidence: 99%

Organic Synthesis: New Vistas in the Brazilian Landscape

Pilli

Assis

2018

An. Acad. Bras. Ciênc.

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In this overview, we present our analysis of the future of organic synthesis in Brazil, a highly innovative and strategic area of research which underpins our social and economical progress. Several different topics (automation, catalysis, green chemistry, scalability, methodological studies and total syntheses) were considered to hold promise for the future advance of chemical sciences in Brazil. In order to put it in perspective, contributions from Brazilian laboratories were selected by the citations received and importance for the field and were benchmarked against some of the most important results disclosed by authors worldwide. The picture that emerged reveals a thriving area of research, with new generations of well-trained and productive chemists engaged particularly in the areas of green chemistry and catalysis. In order to fulfill the promise of delivering more efficient and sustainable processes, an integration of the academic and industrial research agendas is to be expected. On the other hand, academic research in automation of chemical processes, a well established topic of investigation in industrial settings, has just recently began in Brazil and more academic laboratories are lining up to contribute. All these areas of research are expected to enable the future development of the almost unchartered field of scalability.

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Zinc barbier reaction of propargyl halides in water

Cited by 44 publications

References 13 publications

Highly Selective Barbier‐Type Propargylations and Allenylations Catalyzed by Titanocene(III)

Highly Selective Barbier‐Type Propargylations and Allenylations Catalyzed by Titanocene(III)

3-(2,4-Dichlorophenyl)-3-hydroxy-1-phenylpropan-1-one

Organic Synthesis: New Vistas in the Brazilian Landscape

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