Ni-Catalyzed Enantioselective Benzylation of Secondary Phosphine Oxide

A nickel-catalyzed benzylic substitution of secondary phosphine oxide was described, affording the dialkylated P-stereogenic tertiary phosphine oxides with high to excellent enantioselectivities. The reaction was performed under mild conditions with commercially available benzyl chlorides and bench...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 5; pp. 1258 - 1262
Main Authors Cai, Wen-Qiang, Wei, Qi, Zhang, Qing-Wei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 11.02.2022
Amer Chemical Soc
Subjects
benzylation
Chemistry
Chemistry, Organic
enantioselectivity
phosphine
Physical Sciences
Science & Technology
SUBSTITUTION
LIGANDS
ARYLATION
BOND FORMATION
EFFICIENT ASYMMETRIC-SYNTHESIS
ARYL
P-STEREOGENIC PHOSPHINES
CHIRAL PHOSPHINES
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ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/acs.orglett.2c00209

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Summary:A nickel-catalyzed benzylic substitution of secondary phosphine oxide was described, affording the dialkylated P-stereogenic tertiary phosphine oxides with high to excellent enantioselectivities. The reaction was performed under mild conditions with commercially available benzyl chlorides and bench stable secondary phosphine oxides, exhibiting broad functional group tolerance. It represented a practical example for the preparation of P-stereogenic phosphine compounds.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.2c00209