90-11-9Relevant articles and documents
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Corral et al.
, p. 151,157 (1957)
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Hydrogen-Bond-Donor Solvents Enable Catalyst-Free (Radio)-Halogenation and Deuteration of Organoborons
Yang, Yi,Gao, Xinyan,Zeng, Xiaojun,Han, Junbin,Xu, Bo
supporting information, p. 1297 - 1300 (2020/12/23)
A hydrogen bond donor solvent assisted (radio)halogenation and deuteration of organoborons has been developed. The reactions exhibited high functional group tolerance and needed only an ambient atmosphere. Most importantly, compared to literature methods, our conditions are more consistent with the principals of green chemistry (e.g., metal-free, strong oxidant-free, more straightforward conditions).
Direct bromodeboronation of arylboronic acids with CuBr2 in water
Tang, Yan-Ling,Xia, Xian-Song,Gao, Jin-Chun,Li, Min-Xin,Mao, Ze-Wei
supporting information, (2021/01/05)
An efficient and practical method has been developed for the preparation of aryl bromides via the direct bromodeboronation of arylboronic acids with CuBr2 in water. This strategy provides several advantages, such as being ligand-free, base-free, high yielding, and functional group tolerant.
Electrocatalytic Deuteration of Halides with D2O as the Deuterium Source over a Copper Nanowire Arrays Cathode
Chong, Xiaodan,Han, Shuyan,Li, Mengyang,Liu, Cuibo,Zhang, Bin
supporting information, p. 18527 - 18531 (2020/08/21)
Precise deuterium incorporation with controllable deuterated sites is extremely desirable. Here, a facile and efficient electrocatalytic deuterodehalogenation of halides using D2O as the deuteration reagent and copper nanowire arrays (Cu NWAs) electrochemically formed in situ as the cathode was demonstrated. A cross-coupling of carbon and deuterium free radicals might be involved for this ipso-selective deuteration. This method exhibited excellent chemoselectivity and high compatibility with the easily reducible functional groups (C=C, C≡C, C=O, C=N, C≡N). The C?H to C?D transformations were achieved with high yields and deuterium ratios through a one-pot halogenation–deuterodehalogenation process. Efficient deuteration of less-active bromide substrates, specific deuterium incorporation into top-selling pharmaceuticals, and oxidant-free paired anodic synthesis of high-value chemicals with low energy input highlighted the potential practicality.