830-02-4Relevant articles and documents
Copper-Catalyzed Stereoselective Defluorinative Borylation and Silylation of gem-Difluoroalkenes
Tan, Dong-Hang,Lin,Ji, Wei-Wei,Zeng, Yao-Fu,Fan, Wen-Xin,Li, Qingjiang,Gao, Hui,Wang, Honggen
, p. 1032 - 1037 (2018)
The copper-catalyzed stereoselective defluorinative borylation and silylation of gem-difluoroalkenes was developed. The protocol led to the exclusive formation of Z type monofluoroalkenyl borons and silanes in generally good efficiency with broad substrat
One-Pot l-Proline-Mediated Stereoselective α-C(sp2)–H Fluorination of α,β-Unsaturated Aldehydes through Methoxyfluorination–Elimination
Zhou, Jiadi,Jiang, Xinpeng,Jin, Can,Guo, Zhicheng,Su, Bin,Su, Weike
, p. 3631 - 3634 (2017/07/22)
A one-pot, two-step l-proline-mediated stereoselective α-C(sp2)–H fluorination of α,β-unsaturated aldehydes towards their corresponding (Z)-α-fluoro-α,β-unsaturated aldehydes has been developed. The first step utilises Selectfluor as a fluorinating agent in CH3NO2/MeOH forming (Z)-α-fluoro-α,β-unsaturated aldehydes and their corresponding dimethyl acetals through methoxyfluorination-elimination. In the second step, water is added to promote the hydrolytic cleavage of the dimethyl acetals. The obtained (Z)-α-fluoro-α,β-unsaturated aldehydes were smoothly reduced to the corresponding alcohols by using NaBH4.
Highly regioselective SN2′ reaction of β-fluoroallylic phosphates with organocopper reagents and its application to the synthesis of fluorine-containing carbocycles
Nihei, Takashi,Kubo, Yusuke,Ishihara, Takashi,Konno, Tsutomu
, p. 110 - 121 (2015/03/04)
Treatment of β-fluoroallyl phosphates with 2.2 equiv. of organocuprates, prepared readily from 2.2 equiv. each of CuCN and organometallics (organolithium reagents, Grignard reagents, and organozinc reagents), in THF at -40 to 0 °C for 0.25 to 24 h gave γ-products in a highly regioselective manner. Thus obtained γ-adducts were subjected to the ring-closing metathesis, the corresponding cyclic fluoroalkenes being afforded in good yields.