4-Quinolylmethyl and 1-Naphthylmethyl as Benzyl-type Protecting Groups of Carboxylic Acids Removable by Homogeneous Palladium-Catalyzed Hydrogenolysis

Boutros, André; Legros, Jean‐Yves; Fiaud, Jean‐Claude

doi:10.1016/s0040-4020(99)01108-4

Cited by 24 publications

(5 citation statements)

References 17 publications

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“…Ammonium formate reduced the (4-quinolinyl)methyl carboxylates 12 into the 4-methylquinoline with Pd(dba) 2 -DPPE catalyst. 39,40 The catalytic hydrogenolysis was applied to the removal of (4-quinolinyl)methyl protection of various carboxylic acids (Scheme 8).…”

Section: Nucleophilic Substitutionmentioning

confidence: 99%

Catalytic Transformations of Benzylic Carboxylates and Carbonates

Kuwano¹

2009

Synthesis

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Benzylic carboxylates and carbonates react with various molecules in the presence of homogeneous palladium or cobalt catalysts. The catalytic transformations occur at the benzylic carbons of the substrates, affording benzylic substitution products. This review surveys the catalytic reactions using benzylic carboxylates and carbonates as substrates. Furthermore, the related studies on (h 3benzyl)metal complexes are summarized in order to facilitate the understanding and consideration of the catalytic substitution. 1 Introduction 2 Chemistry of the (h 3-Benzyl)metal Complex 2.1 Structure of the (h 3-Benzyl)metal Complex 2.2 Reactivity of the (h 3-Benzyl)metal Complex 3 Catalytic Transformations of Benzylic Esters 3.

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Section: Nucleophilic Substitutionmentioning

confidence: 99%

Catalytic Transformations of Benzylic Carboxylates and Carbonates

Kuwano¹

2009

Synthesis

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“…[30] Similarly, desilylation of (E)-27 (nBu 4 NF/THF) followed by double esterification (2 MsCl, NEt 3 ) gave the dimesylate (E)-41e (R ϭ 2-naphthyl, X ϭ OMs) in 70% overall yield. Subsequent attempted palladium(0)-induced {Pd(dba) 2 , dppe} and base-induced (DBU/DMF at 60°C) elimination of MsOH by a reported procedure [38] also failed to provide (E)-39e and 40e (R ϭ 2-naphthyl) (Scheme 5). O-Protection of (E)-37 (DHP, PPTs) quantitatively furnished the tetrahydropyranyl ether (E)-43a (X ϭ OTHP), which was then able to undergo dehydrochlorination (tBuOK/THF at reflux for 12 h) to afford the (E)-2-ethyl-2-ethenylcyclopropanol derivative 44a (X ϭ OTHP) in 85% yield (Scheme 7).…”

Section: (E)-cyclopropanation Of β-Halo Estersmentioning

confidence: 99%

Titanium-Mediated Diastereoselective Formation of (E)- or (Z)-2-Substituted 1-Vinylcyclopropanols: Scope and Limitation, Applications

et al. 2002

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“…4-Quinolylmethyl esters (4-QUI) are reduced by palladiumcatalysed hydrogenolysis using ammonium formate as the reductant. 103 The reaction is best conducted in DMSO at 50 ЊC in which case aromatic bromo compounds, aliphatic chloro compounds, alkenes, aldehydes, and nitriles are inert. However, allyl esters are cleaved selectively under these conditions leaving the 4-QUI ester intact and aromatic nitro compounds are reduced to the aniline derivative.…”

Section: Carboxy Protecting Groupsmentioning

confidence: 99%