7577-09-5Relevant academic research and scientific papers
Cu-Catalyzed Oxidative Allylic C-H Arylation of Inexpensive Alkenes with (Hetero)Aryl Boronic Acids
Pal, Suman,Cotard, Marine,Gérardin, Baptiste,Hoarau, Christophe,Schneider, Cédric
supporting information, p. 3130 - 3135 (2021/05/05)
Herein, we present a regioselective Cu-catalyzed oxidative allylic C(sp3)-H arylation by radical relay using a broad range of heteroaryl boronic acids with inexpensive and readily available unactivated terminal and internal olefins. This C(sp2)-C(sp3) allyl coupling has the advantage of using cheap, abundant, and nontoxic Cu2O without the need to use prefunctionalized alkenes, thus offering an alternative method to allylic arylation reactions that employ more traditional coupling partners with preinstalled leaving groups (LGs) at the allylic position.
Sulfur-mediated allylic C-H arylation, epoxidation, and aziridination
Luo, Hang,Hu, Gang,Li, Pingfan
, p. 10569 - 10578 (2019/09/30)
Transition-metal-free, sulfur-mediated allylic C-H arylation, epoxidation, and aziridination were realized through one-pot procedures. The reaction design involved initial addition between olefins and triflic anhydride activated sulfoxides, followed by subsequent reactions of the allylic sulfur ylides generated under basic conditions with arylboronic acids, aldehydes, or aldimines, to give allylic arylation, epoxidation, or aziridination products, respectively.
Selective catalytic C-H alkylation of alkenes with alcohols
Lee, Dong-Hwan,Kwon, Ki-Hyeok,Yi, Chae S.
scheme or table, p. 1613 - 1616 (2012/02/01)
Alkenes and alcohols are among the most abundant and commonly used organic feedstock in industrial processes. We report a selective catalytic alkylation reaction of alkenes with alcohols that forms a carbon-carbon bond between vinyl carbon-hydrogen (C-H) and carbon-hydroxy centers with the concomitant loss of water. The cationic ruthenium complex [(C6H6)(PCy 3)(CO)RuH]+BF4- (Cy, cyclohexyl) catalyzes the alkylation in solution within 2 to 8 hours at temperatures ranging from 75° to 110°C and tolerates a broad range of substrate functionality, including amines and carbonyls. Preliminary mechanistic studies are inconsistent with Friedel-Crafts-type electrophilic activation of the alcohols, suggesting instead a vinyl C-H activation pathway with opposite electronic polarization.
