101025-08-5Relevant articles and documents
Air-Stable PdI Dimer Enabled Remote Functionalization: Access to Fluorinated 1,1-Diaryl Alkanes with Unprecedented Speed
Kundu, Gourab,Opincal, Filip,Schoenebeck, Franziska,Sperger, Theresa
, (2021/11/30)
While remote functionalization via chain walking has the potential to enable access to molecules via novel disconnections, such processes require relatively long reaction times and can be in need of elevated temperatures. This work features a remote arylation in less than 10 min reaction time at room temperature over a distance of up to 11 carbons. The unprecedented speed is enabled by the air-stable PdI dimer [Pd(μ-I)(PCy2tBu)]2, which in contrast to its PtBu3 counterpart does not trigger direct coupling at the initiation site, but regioconvergent and chemoselective remote functionalization to yield valuable fluorinated 1,1-diaryl alkanes. Our combined experimental and computational studies rationalize the origins of switchability, which are primarily due to differences in dispersion interactions.
Synthesis and Identification of ω-Phenylalkylcatechols in Burmese Lac
Jefferson, Alan,Sargent, Melvyn V.,Wangchareontrakul, Sirichai
, p. 19 - 25 (2007/10/02)
The presence of 3-(10'-phenyldecyl)- (2) (2percent), 3-(12'-phenyldodecyl)- (3) (6percent), 4-(10'-phenyldecyl)- (4) (0.3percent) and 4-(12'-phenyldodecyl)-benzene-1,2-diol (5) (0.3percent) in Burmese lac, the sap of Melanorrhoea usitata Wall has been confirmed by the synthesis of these compounds and a comparison of the gas chromatographic retention times and the mass spectral characteristic of their bis-O-(trimethylsilyl) derivatives with the derivatives of the natural products.Typically, 3,4-bis(benzyloxy)benzaldehyde (7) on Wittig reaction with triphenyl(11-phenylundecyl)phosphonium bromide (20) and subsequent catalytic hydrogenation of the resultant olefin gave compound (5) in 59percent overall yield.