Literature DB >> 18808127

An improved protocol for the Pd-catalyzed alpha-arylation of aldehydes with aryl halides.

Rubén Martín1, Stephen L Buchwald.   

Abstract

An improved protocol for the Pd-catalyzed alpha-arylation of aldehydes with aryl halides has been developed. The new catalytic system allows for the coupling of an array of substrates including challenging electron-rich aryl bromides and less reactive aryl chlorides. The utility of this method has been demonstrated in a new total synthesis of (+/-)-sporochnol.

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Year:  2008        PMID： 18808127      PMCID： PMC2748776          DOI： 10.1021/ol8017775

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


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2.  Stable cyclic (alkyl)(amino)carbenes as rigid or flexible, bulky, electron-rich ligands for transition-metal catalysts: a quaternary carbon atom makes the difference.

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4.  A general method for the direct alpha-arylation of aldehydes with aryl bromides and chlorides.

Authors:  Rubén Martín; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

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8.  Palladium-catalyzed alpha-arylation of carbonyl compounds and nitriles.

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9.  Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig reactions.

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Journal:  J Am Chem Soc       Date:  2006-03-29       Impact factor: 15.419

10.  Palladium-catalyzed alpha-arylation of aldehydes with bromo- and chloroarenes catalyzed by [{Pd(allyl)Cl}2] and dppf or Q-phos.

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  9 in total

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5.  On the stereochemical course of palladium-catalyzed cross-coupling of allylic silanolate salts with aromatic bromides.

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6.  Selective monoarylation of acetate esters and aryl methyl ketones using aryl chlorides.

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7.  Investigating the dearomative rearrangement of biaryl phosphine-ligated Pd(II) complexes.

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8.  Replacing conventional carbon nucleophiles with electrophiles: nickel-catalyzed reductive alkylation of aryl bromides and chlorides.

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9.  Chromium-catalyzed para-selective formation of quaternary carbon centers by alkylation of benzamide derivatives.

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  9 in total

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