Regio- and stereoselective hydrosulfonylation of conjugated dienes via (.pi.-allyl)palladium complex

Tamaru, Yoshinao; Yamada, Yoshimi; Kagotani, M.; Ochiai, Hideo; Nakajo, Eiji; Suzuki, Ryoshu; Yoshida, Zen‐ichi

doi:10.1021/jo00172a043

Cited by 14 publications

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“…In an early representative example, Yoshida and co-workers demonstrated that stabilized π-allylpalladium complexes could also be accessed by treatment of conjugated dienes with stoichiometric amounts of PdCl 2 and a suitable nucleophile (Scheme 28). 74 Protodepalladation of these complexes with dimethylglyoxime in a protic solvent cleanly afforded sulfonylated Z -alkenes, presumably due to coordination of the sulfonyl group to palladium.…”

Section: Examples Of Synthetically Enabling Protodepalladation Reactionsmentioning

confidence: 99%

Protodepalladation as a Strategic Elementary Step in Catalysis

O’Duill

Engle

2018

Synthesis

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Protodepalladation is the redox-neutral conversion of a C-Pd(II) bond to a C-H bond promoted by a Brønsted acid. It can be viewed as the microscopic reserves of Pd(II)-mediated C-H cleavage. In the context of catalytic reaction development, protodepalladation offers a means of converting organopalladium(II) intermediates to organic products without a change in oxidation state at the metal center. Hence, when integrated into catalytic cycles, it can be a uniquely enabling elementary step. The goal of this Review is to provide an overview of protodepalladation, including exploration of different reactions types, discussion of literature examples, and analysis of mechanistic features. Our hope is that this review will stimulate other researchers in the field to pursue new applications of this underexploited step in catalysis.

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Section: Examples Of Synthetically Enabling Protodepalladation Reactionsmentioning

confidence: 99%

Protodepalladation as a Strategic Elementary Step in Catalysis

O’Duill

Engle

2018

Synthesis

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[4 + 2]‐Cycloadditionen mit 5‐Ethenyl‐3,4‐dihydro‐2H‐pyran und 5‐Ethenyl‐2,3‐dihydro‐1,4‐dioxin

Potthoff

Breitmaier

1986

Chem. Ber.

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4 + 2]-Cycloadditions with 5-Ethenyl-3,4dihydro-2H-pyran and 5Ethenyl-2,3-dihydro-l,4dioxine S-Ethenyl-3,4-dihydro-2H-pyran (2a) and 5-ethenyl-2,3-dihydro-l,4dioxine (2 b) as heterocyclic donor-activated 1,3-dienes are prepared by Wittig alkenylation of the aldehydes l a and 1 b. [4 + 21-Cycloadditions with dienophiles such as tetracyanoethene, p-nitrostyrene, diethyl azodicarboxylate, phenyltriazolinedione, and diethyl mesoxalate yield the new heterobi-and -tricycles 3-7. a: X = CH2 b : X = O l a , b 40 A0A 0 20, b 7 6 a , b N II N C02C2H5 5 a , b 0 VCH Verlagsgesellschaft mbH, D-6940 Weinheim, 1986

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Cu‐Catalyzed Formal Methylative and Hydrogenative Carboxylation of Alkynes with Carbon Dioxide: Efficient Synthesis of α,β‐Unsaturated Carboxylic Acids

Takimoto

Hou

2013

Chemistry A European J

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The sequential hydroalumination or methylalumination of various alkynes catalyzed by different catalyst systems, such those based on Sc, Zr, and Ni complexes, and the subsequent carboxylation of the resulting alkenylaluminum species with CO2 catalyzed by an N-heterocyclic carbene (NHC)-copper catalyst have been examined in detail. The regio- and stereoselectivity of the overall reaction relied largely on the hydroalumination or methylalumination reactions, which significantly depended on the catalyst and alkyne substrates. The subsequent Cu-catalyzed carboxylation proceeded with retention of the stereoconfiguration of the alkenylaluminum species. All the reactions could be carried out in one-pot to afford efficiently a variety of α,β-unsaturated carboxylic acids with well-controlled configurations, which are difficult to construct by previously reported methods. This protocol could be practically useful and attractive because of its high regio- and stereoselectivity, simple one-pot reaction operation, and the use of CO2 as a starting material.

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Regio- and stereoselective hydrosulfonylation of conjugated dienes via (.pi.-allyl)palladium complex

Abstract: 1) Preliminary accounts of this paper: (a) T a m m , Y.; Kagotani, M.; Yoshida, Z. (2) (a) Block, E. 'Reactions of Organosulfur Compounds"; Academic P r w : New York, 1978. (b) Trost, B. M.; Melvin, L. S., Jr. "Sufur Ylides"; R 2 R3 R4 reaction conditionsC yield,d %) (isolated yield,e %)

Cited by 14 publications

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Protodepalladation as a Strategic Elementary Step in Catalysis

Protodepalladation as a Strategic Elementary Step in Catalysis

[4 + 2]‐Cycloadditionen mit 5‐Ethenyl‐3,4‐dihydro‐2H‐pyran und 5‐Ethenyl‐2,3‐dihydro‐1,4‐dioxin

Cu‐Catalyzed Formal Methylative and Hydrogenative Carboxylation of Alkynes with Carbon Dioxide: Efficient Synthesis of α,β‐Unsaturated Carboxylic Acids

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