334015-45-1Relevant articles and documents
Sequential Energy Transfer Catalysis: A Cascade Synthesis of Angularly-Fused Dihydrocoumarins
Nevesely, Tomá?,Daniliuc, Constantin G.,Gilmour, Ryan
, p. 9724 - 9728 (2019)
An operationally simple one-pot protocol has been developed to enable the conversion of diversely substituted cinnamic acid derivatives into angularly-fused dihydrocoumarins (up to 94%). Inspired by coumarin biosynthesis, this reaction cascade harnesses photochemical E → Z alkene isomerization enabled by energy transfer catalysis using inexpensive thioxanthen-9-one (TX) under irradiation at 402 nm. Subsequent lactonization generates the heterocyclic core prior to a second photosensitization event to induce a [2 + 2] cycloaddition, again mediated by TX. The tetracyclic products are generated efficiently, and proof of the structure was established by X-ray crystallography. Mechanistic investigations, including structural probes and NMR reaction monitoring, support the postulated order of events. The study underscores the synthetic value of inexpensive small-molecule organic photocatalysts in the generation of structural complexity via sequential ?€-bond activation.
Regioselective formylation of 1,3-disubstituted benzenes through in situ lithiation
Wang, Le,Wang, Yan,Guo, Fangxu,Zheng, Yue,Bhadury, Pinaki S.,Sun, Zhihua
supporting information, p. 6053 - 6056 (2013/10/22)
A facile method of regioselective formylation of disubstituted benzene via in situ deprotonation/metalation using n-BuLi/TMEDA/DIPA has been developed. Effect of different electron withdrawing and electron donating substituents in 1,3-interrelated aromatic system was studied; the metalation mostly occurred at the 2-position to afford the desired products in high yields.