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Palladium-catalyzed, aminoquinoline-directed arylation of phosphonamidate and phosphinic amide sp3 C-H bonds.

ABSTRACT: Aminoquinoline-directed, palladium-catalyzed sp3 C-H bond arylation in phosphonamidates and phosphinic amides is reported. The reaction employs Pd(OAc)2 as a catalyst at 10 mol% loading and cesium phosphate or potassium carbonate as a base in 1,2-dichlorobenzene as a solvent. The directing group can be removed under basic conditions to afford phosphonic acid esters. The chemistry described here is the first example of unactivated sp3 C-H bond arylation by using a phosphorus-containing directing group.

SUBMITTER: Nguyen TT

PROVIDER: S-EPMC5479433 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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Palladium-catalyzed, aminoquinoline-directed arylation of phosphonamidate and phosphinic amide sp3 C-H bonds.

Nguyen Tung Thanh TT Nguyen Tung Thanh TT Daugulis Olafs O

Chemical communications (Cambridge, England) 20170401 33

Aminoquinoline-directed, palladium-catalyzed sp3 C-H bond arylation in phosphonamidates and phosphinic amides is reported. The reaction employs Pd(OAc)2 as a catalyst at 10 mol% loading and cesium phosphate or potassium carbonate as a base in 1,2-dichlorobenzene as a solvent. The directing group can be removed under basic conditions to afford phosphonic acid esters. The chemistry described here is the first example of unactivated sp3 C-H bond arylation by using a ...[more]

PMID: 28394374

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