25882-22-8Relevant academic research and scientific papers
Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions
Costello, Jeff P.,Ferreira, Eric M.
supporting information, p. 9934 - 9939 (2019/12/24)
The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization of the alkyne that leads to preferential heteroatom attack at the more electron-deficient carbon. The electronic effects are studied in other contexts, including hydroacyloxylation and hydroamination, and similar trends in directionality are predominant although not uniformly observed.
Direct catalytic cross-coupling of alkenyllithium compounds
Hornillos, Valentn,Giannerini, Massimo,Vila, Carlos,Faans-Mastral, Martn,Feringa, Ben L.
, p. 1394 - 1398 (2015/02/19)
A catalytic method for the direct cross-coupling of alkenyllithium reagents with aryl and alkenyl halides is described. The use of a catalyst comprising Pd2(dba)3/XPhos allows for the stereoselective preparation of a wide variety of substituted alkenes in high yields under mild conditions. In addition (1-ethoxyvinyl)lithium can be efficiently converted into substituted vinyl ethers which, after hydrolysis, give readily access to the corresponding methyl ketones in a one pot procedure.
Preparation of C-arylglycals via Suzuki–Miyaura cross-coupling of dihydropyranylphosphates
Leidy, Michelle R.,Mason Hoffman,Pongdee, Rongson
supporting information, p. 6889 - 6891 (2019/04/10)
The preparation of C-arylglycals has been accomplished by employing the Suzuki–Miyaura cross-coupling reaction of dihydropyranylphosphates with arylboronate esters. The reaction is tolerant of both electron-donating (EDG) and electron-withdrawing (EWG) gr
Suzuki-Miyaura cross-coupling of α-phosphoryloxy enol ethers with arylboronic acids
Pedzisa, Lee,Vaughn, Ian W.,Pongdee, Rongson
, p. 4142 - 4144 (2008/09/20)
The Suzuki-Miyaura cross-coupling reaction of cyclic ketene acetal phosphates with arylboronic acids was found to be a convenient and highly efficient method for the construction of aryl vinyl ethers. A wide variety of differentially substituted electron-poor and electron-rich arylboronic acids smoothly underwent the coupling process to provide the desired dihydropyrans in moderate to excellent yields.
Palladium-catalyzed cross-coupling reactions between dihydropyranylindium reagents and aryl halides. Synthesis of C-aryl glycals
Lehmann, Ute,Awasthi, Smita,Minehan, Thomas
, p. 2405 - 2408 (2007/10/03)
(Matrix presented) Palladium(0)-catalyzed cross-coupling reactions between tris(dihydropyranyl)indium 1 and aryl halides 2 have been investigated. Aryl iodides and electron-deficient aryl bromides couple efficiently with the in situ-generated indium reage
