Palladium/benzoic acid-catalyzed hydroalkoxylation of alkynes

Kadota, Isao; Lutete, Léopold Mpaka; Shibuya, Atsushi; Yamamoto, Yoshinori

doi:10.1016/s0040-4039(01)01207-2

Cited by 102 publications

(51 citation statements)

References 15 publications

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“…The corresponding cinnamyl ethers are obtained in good to excellent yields (82-96 %; Scheme 59). [185] The mechanism of this reaction is similar to the hydroamination of alkynes, in which the reaction proceeds by the palladium/benzoic acid-catalyzed isomerization of the alkyne to the allene, followed by the addition of alcohols to the pallylpalladium intermediate formed by the hydropalladation of the resulting allene. Acidic alcohols undergo regioselective trans addition to conjugated diynes in the presence of a Pd 0 catalyst to form the corresponding monohydroalkoxylated product (Scheme 60).…”

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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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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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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“…Alcohols have also proven to be suitable reagents towards the synthesis of the cyclic ether products, in the presence of palladium and gold catalysts [43][44][45][46]. Diastereoselective zinc-catalyzed alkynylation of α-bromo oxocarbenium ions to synthesize trans-α-alkynyl-β-halo pyran and furan derivatives is known [47].…”

Section: Introductionmentioning

confidence: 99%

Brønsted Acid-Catalyzed Direct Substitution of 2-Ethoxytetrahydrofuran with Trifluoroborate Salts

Fisher

Bolshan

2016

Catalysts

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Metal-free transformations of organotrifluoroborates are advantageous since they avoid the use of frequently expensive and sensitive transition metals. Lewis acid-catalyzed reactions involving potassium trifluoroborate salts have emerged as an alternative to metal-catalyzed protocols. However, the drawbacks to these methods are that they rely on the generation of unstable boron dihalide species, thereby resulting in low functional group tolerance. Recently, we discovered that in the presence of a Brønsted acid, trifluoroborate salts react rapidly with in situ generated oxocarbenium ions. Here, we report Brønsted acid-catalyzed direct substitution of 2-ethoxytetrahydrofuran using potassium trifluoroborate salts. The reaction occurs when tetrafluoroboric acid is used as a catalyst to afford functionalized furans in moderate to excellent yields. A variety of alkenyl-and alkynyltrifluoroborate salts readily participate in this transformation.

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“…These are usually sufficiently electrophilic for nucleophilic attack by water [2], alcohol [3,4], phenols [5], amines [6,7] and many other nucleophiles. A wide variety of transition metal based catalysts have been reported to catalyze alkyne hydration [8], alkynylaryl amine [9][10][11][12][13][14][15] and -phenol [16][17][18][19] cyclization, etc.…”

Section: Introductionmentioning

confidence: 99%

One-Pot Formation of Functionalized Indole and Benzofuran Derivatives Using a Single Bifunctional Ruthenium Catalyst

2010

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Palladium/benzoic acid-catalyzed hydroalkoxylation of alkynes

Cited by 102 publications

References 15 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

Brønsted Acid-Catalyzed Direct Substitution of 2-Ethoxytetrahydrofuran with Trifluoroborate Salts

One-Pot Formation of Functionalized Indole and Benzofuran Derivatives Using a Single Bifunctional Ruthenium Catalyst

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