54774-82-2Relevant articles and documents
Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols
Ganiu, Moshood O.,Cleveland, Alexander H.,Paul, Jarrod L.,Kartika, Rendy
supporting information, p. 5611 - 5615 (2019/08/01)
The utility of triphosgene and DMAP as mild reagents for chemoselective dehydration of tertiary alcohols is reported. Performed in dichloromethane at room temperature, this reaction is readily tolerated by a broad scope of substrates, yielding alkenes preferentially with the (E)-geometry. While formation of the Hofmann products is generally favored, a dramatic change in alkene selectivity toward the Zaitzev products is observed when the reaction is carried out in dichloroethane at reflux.
Copper-catalyzed alkene arylation with diaryliodonium salts
Phipps, Robert J.,McMurray, Lindsay,Ritter, Stefanie,Duong, Hung A.,Gaunt, Matthew J.
supporting information; experimental part, p. 10773 - 10776 (2012/08/07)
Alkenes and arenes represent two classes of feedstock compounds whose union has fundamental importance to synthetic organic chemistry. We report a new approach to alkene arylation using diaryliodonium salts and Cu catalysis. Using a range of simple alkenes, we have shown that the product outcomes differ significantly from those commonly obtained by the Heck reaction. We have used these insights to develop a number of new tandem and cascade reactions that transform readily available alkenes into complex arylated products that may have broad applications in chemical synthesis.
Aerobic alcohol oxidation coupled to palladium-catalyzed alkene hydroarylation with boronic esters
Iwai, Yasumasa,Gligorich, Keith M.,Sigman, Matthew S.
, p. 3219 - 3222 (2008/12/23)
(Chemical Equation Presented) An oxidation exercise: An aerobic alcohol oxidation coupled with a regioselective palladium-catalyzed reductive functionalization of styrenes and arylboronic esters has been developed (see scheme). The mechanism is thought to proceed by initial oxidation of the solvent to generate a PdII-hydride species, which subsequently reacts with the alkene and arylboronic ester to ultimately generate a new C-C bond.