186083-47-6Relevant articles and documents
Reaction rate differences between organotrifluoroborates and boronic acids in BINOL-catalyzed conjugate addition to enones
Brooks, Bailey,Hiller, Noemi,May, Jeremy A.
, (2021/09/28)
Enantioselective organocatalysis has been successfully employed in combination with trifluoroborate reagents for novel organic transformations over the last decade. However, no experimental rate studies of these reactions have been reported. Herein we report Hammett plot analysis of the organocatalyzed enantioselective conjugate addition of alkenyl, aryl, and heteroaryl trifluoroborate salts to chalcone derivatives with substitution at both the β-aryl and keto-aryl positions. The rate trend for keto-aryl substitution diverges from that of boronic acid nucleophiles in that the keto-aryl substituent for trifluoroborate salts does not measurably impact reaction rate in a manner consistent with charge stabilization. In addition, variable temperature NMR in combination with quantitative thin-layer chromatography (TLC) analysis suggests that the reaction is impacted by the low solubility of the trifluoroborate salts, so particle size and stirring speed affect reaction rates.
Decarboxylative substitution of β-keto acids to benzylic alcohols catalyzed by molecular iodine
Han, Fuzhong,Zhang, Xinxin,Hu, Minggang,Jia, Lina
, p. 11466 - 11471 (2015/12/04)
An efficient method for molecular iodine catalyzed decarboxylative substitution of β-keto acids with benzylic alcohols under mild conditions has been described and valuable α-functionalized ketones were obtained in good to excellent yields.
Triflic acid promoted direct α-alkylation of unactivated ketones using benzylic alcohols via in situ formed acetals
Koppolu, Srinivasa Rao,Naveen, Naganaboina,Balamurugan, Rengarajan
, p. 6069 - 6078 (2014/07/21)
Direct α-alkylation of unactivated ketones using benzylic alcohols as electrophiles has been achieved at room temperature. This reaction takes place via in situ formed acetal using triflic acid and trimethyl orthoformate. It is believed that methyl vinyl