612042-30-5Relevant academic research and scientific papers
Visible-Light-Induced Palladium-Catalyzed Selective Defluoroarylation of Trifluoromethylarenes with Arylboronic Acids
He, Chun-Yang,Luo, Yun-Cheng,Tong, Fei-Fei,Zhang, Xingang,Zhang, Yanxia
, p. 13971 - 13979 (2021)
Selective functionalization of inactive C(sp3)-F bonds to prepare medicinally interesting aryldifluoromethylated compounds remains challenging. One promising route is the transition-metal-catalyzed cross-coupling through oxidative addition of the C(sp3)-F bond in trifluoromethylarenes (ArCF3), which are ideal precursors for this process due to their ready availability and low cost. Here, we report an unprecedented excited-state palladium catalysis strategy for selective defluoroarylation of trifluoromethylarenes with arylboronic acids. This visible-light-induced palladium-catalyzed cross-coupling proceeds under mild reaction conditions and allows transformation of a variety of arylboronic acids and ArCF3. Preliminary mechanistic studies reveal that the oxidative addition of the C(sp3)-F bond in ArCF3 to excited-state palladium(0) via a single electron transfer pathway is responsible for the C(sp3)-F bond activation.
Directed ortho -metalation-cross-coupling strategies. One-pot Suzuki reaction to biaryl and heterobiaryl sulfonamides
Schneider, Cedric,Broda, Ellen,Snieckus, Victor
supporting information; experimental part, p. 3588 - 3591 (2011/10/03)
A general synthesis of stable ortho-boropinacolato aryl and heteroaryl sulfonamides by directed ortho-metalation (DoM) and either MeOBPin or i-PrOBpin electrophile quench, 3 → 4, is described. A one-pot metalation-Suzuki cross-coupling procedure for the synthesis of biaryls and heterobiaryls, 3 → 5, and a complementary DoM-Ir-catalyzed boronation sequence (Scheme 6) are delineated.
