683229-61-0Relevant articles and documents
Metal-Free Arene and Heteroarene Borylation Catalyzed by Strongly Electrophilic Bis-boranes
Liu, Yun-Lin,Kehr, Gerald,Daniliuc, Constantin G.,Erker, Gerhard
, p. 12141 - 12144 (2017)
The geminal chelate bis-borylalkanes 4 and 5 featuring strongly electrophilic B(C6F5)2 and B(C6F5) groups, respectively, serve as efficient catalysts for the borylation of arenes and heteroarenes. The
Preparation method of benzoheterocyclic-3-boric acid
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Paragraph 0012; 0031; 0033, (2021/03/31)
The invention discloses a preparation method of benzoheterocycle-3-boric acid, and belongs to the technical field of organic boric acid chemistry. The method comprises the following steps: starting from benzoheterocycle, carrying out selective Friedel-Crafts reaction on benzoheterocycle and boron trihalide in the presence of a catalyst, and carrying out hydrolyzing to obtain benzoheterocycle-3-boric acid. According to the method, proper catalysts and reaction conditions are selected, boric acid is obtained after high-selectivity positioning and hydrolysis are conducted on the heterocycle 3 position, and the benzoheterocycle-3-boric acid is obtained after purification by means of the property difference of the boric acid on the 2 position and the boric acid on the 3 position. The method provides a simple synthesis path for benzoheterocycle-3-boric acid, and has the advantages of high yield and easy isomer purification.
Organophosphorus-catalyzed relay oxidation of H-Bpin: electrophilic C-H borylation of heteroarenes
Lipshultz, Jeffrey M.,Fu, Yue,Liu, Peng,Radosevich, Alexander T.
, p. 1031 - 1037 (2021/02/06)
A nontrigonal phosphorus triamide (1, P{N[o-NMe-C6H4]2}) is shown to catalyze C-H borylation of electron-rich heteroarenes with pinacolborane (HBpin) in the presence of a mild chloroalkane reagent. C-H borylation proceeds for a range of electron-rich heterocycles including pyrroles, indoles, and thiophenes of varied substitution. Mechanistic studies implicate an initial P-N cooperative activation of HBpin by1to giveP-hydrido diazaphospholene2, which is diverted by Atherton-Todd oxidation with chloroalkane to generateP-chloro diazaphospholene3. DFT calculations suggest subsequent oxidation of pinacolborane by3generates chloropinacolborane (ClBpin) as a transient electrophilic borylating species, consistent with observed substituent effects and regiochemical outcomes. These results illustrate the targeted diversion of established reaction pathways in organophosphorus catalysis to enable a new mode of main group-catalyzed C-H borylation.