Palladium/Benzoic Acid Catalyzed Hydroamination of Alkynes

The regioselective functionalization of terminal alkenes and alkynes is of utmost importance for the synthesis of a wide variety of organic products. Based on the original observation by Vladimir Markovnikov-the pioneer of this field of research-in the 19th century, the possible regioisomeric products are classified as Markovnikov or anti-Markovnikov products. Contrary to traditional belief, it is nowadays possible to control the regiochemistry of various additions of nucleophiles to alkenes and alkynes by applying different transition-metal catalysts. Recent developments in this area of selective functionalization of alkenes and alkynes are reviewed.

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“…[146] For example, 1-phenyl-1-propyne reacts with dibenzylamine in dioxane at 100 8C to give the corresponding allylamine (98 % yield).…”

Section: Angewandte Chemiementioning

confidence: 99%

Catalytic Markovnikov and anti‐Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends

et al. 2004

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“…In 1999, Yamamoto discovered that the intramolecular hydroamination of allenes could be accomplished from aminoalkyne starting materials, through in situ formation of the allene 107 (Scheme 45) [87]. Further investigations of this system have since been reported [88], including expansions of scope to generate lactams [89] and tetrahydroisoquinolines [90] (Scheme 45), as well as asymmetric variants discussed in Sect.…”

Section: Palladium-and Platinum-catalyzed Reactionsmentioning

confidence: 99%

Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Hydroamination or Hydroalkoxylation Reactions

Julian

2013

Topics in Heterocyclic Chemistry

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The intramolecular hydrofunctionalization of carbon-carbon multiple bonds has emerged as a powerful way to form cyclic structures. A particularly important class of reactions involves the use of amine or alcohol nucleophiles, and alkenes or allenes as electrophiles, to form pyrrolidine, piperidine, tetrahydrofuran, and tetrahydropyran heterocycles in a highly efficient manner using late transition metal catalysts. Asymmetric methods for hydroamination and hydroalkoxylation reactions have recently emerged, allowing for the enantioselective synthesis of such saturated heterocycles. This review covers recent developments (over the last 5-10 years) in late transition metal-catalyzed hydroamination and hydroalkoxylation reactions that generate saturated heterocycles.

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“…For metal carbene N À H insertions, a-diazocarbonyl compounds normally serve as metal carbene precursors, and Cu(I) and Rh(II) complexes are the most widely used catalysts. While for hydroamination of alkynes, transition metal complexes of Ti, [8] Pd, [9] Pt, [10] Ru, [11] Au, [12] Rh, [13] Ir, [14] La, [7f,15] Zn and Cd, [16] Hg, [17] Zr [18] and Ac [19] have been widely utilized. Although it is less common, copper-catalyzed hydroamination of alkynes has also been reported.…”

Section: Introductionmentioning

confidence: 99%

Sequential Copper(I)‐Catalyzed Reaction of Amines with o‐Acetylenyl‐Substituted Phenyldiazoacetates

2008

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Palladium/Benzoic Acid Catalyzed Hydroamination of Alkynes

Cited by 160 publications

References 12 publications

Catalytic Markovnikov and anti‐Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends

Catalytic Markovnikov and anti‐Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends

Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Hydroamination or Hydroalkoxylation Reactions

Sequential Copper(I)‐Catalyzed Reaction of Amines with o‐Acetylenyl‐Substituted Phenyldiazoacetates

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