Zinc Chloride Enhanced Arylations of Secondary Benzyl Trifluoroacetates in the Presence of β‐Hydrogen Atoms

Abstract

Zinc or swim: Arylation of benzyl trifluoroacetates with arylzinc reagents in the presence of β‐hydrogen atoms were realized under mild conditions. Both electron‐rich and electron‐deficient arene substrates were successfully arylated. This arylation method could offer a very versatile synthetic route to access a series of diversity‐oriented diarylalkane motifs. TFA = trifluoroacetyl.

Catalytic Borylation using an Air‐Stable Zinc Boryl Reagent: Systematic Access to Elusive Acylboranes

“…Infrared bands in the range 1610-1640 cm À1 were observed for the acyl group,c onsistent with that reported for 8a (1618 cm À1 ). [20] Thus,bromobenzene (4a)and benzoylchloride (7a)w ere converted into the phenylborane 5a and benzoylborane 8a,respectively,inyields essentially identical to those obtained using isolated samples of 3.Asimple one-pot procedure for the synthesis of acyl boranes is therefore feasible using materials which can be manipulated easily under bench-top conditions. As with 8a, [11] theC ÀObond lengths [8h: 1.229(3) ; 8k:1.234(4) ] are slightly longer than those found in related ketones, presumably because of the strong s-donor character of the boryl substituent.…”

Iron‐Catalyzed Arylation of Aromatic Ketones and Aldehydes Mediated by Organosilanes

“…R f = 0.57 (dichloromethane/hexane, 1:3). Characterization data is consistent with that published previously 28…”

Protodeboronation of Tertiary Boronic Esters: Asymmetric Synthesis of Tertiary Alkyl Stereogenic Centers

“…22 The method also provides access to highly enantioenriched deuterated tertiary alkanes by simply substituting H 2 O for D 2 O. The utility of the methodology has been illustrated in a short and highly enantioselective synthesis of (S)-turmerone.…”