919767-83-2Relevant academic research and scientific papers
Stereoselective Desymmetrization of gem-Diborylalkanes by “Trifluorination”
Kumar, Nivesh,Reddy, Reddy Rajasekhar,Masarwa, Ahmad
, p. 8008 - 8012 (2019/05/28)
An efficient and general method for the chemoselective synthesis of unsymmetrical gem-diborylalkanes is reported. This method is based on a late-stage desymmetrization through nucleophilic “trifluorination”, providing chiral gem-diborylalkanes bearing a trifluoroborate group. The reaction offers a highly modular and diastereoselective approach towards the synthesis of gem-diborylcyclopropanes. The utility of the gem-diborylalkane building blocks was demonstrated by selective post-functionalization of the trifluoroborate group. These functionalizations include inter- and intra- Pd-catalyzed Suzuki–Miyaura coupling reactions.
A Modular Approach to the Synthesis of gem-Disubstituted Cyclopropanes
Harris, Michael R.,Wisniewska, Hanna M.,Jiao, Wenhua,Wang, Xiaochun,Bradow, James N.
, p. 2867 - 2871 (2018/05/29)
A diastereoselective, Pd-catalyzed Suzuki-Miyaura coupling reaction of geminal bis(boryl)cyclopropanes has been developed. The reaction offers a highly modular approach to the synthesis of tertiary cyclopropylboronic esters. The resulting boronic esters may be further functionalized to afford a range of gem-disubstituted cyclopropanes, which represent an important structural motif in the pharmaceutical industry. Sequential Suzuki-Miyaura cross-coupling reactions of gem-bis(boryl)cyclopropanes are also reported. The coupling protocols are compatible with a broad range of functionalized aryl and heteroaryl bromides.
Simple access to elusive α-boryl carbanions and their alkylation: An umpolung construction for organic synthesis
Hong, Kai,Liu, Xun,Morken, James P.
supporting information, p. 10581 - 10584 (2014/08/18)
The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds. The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carbanion.
Synthesis and applications of 1,1-diborylated cyclopropanes: Facile route to 1,2-diboryl-3-methylenecyclopentenes
Shimizu, Masaki,Schelper, Michael,Nagao, Ikuhiro,Shimono, Katsuhiro,Kurahashi, Takuya,Hiyama, Tamejiro
, p. 1222 - 1223 (2008/02/03)
Cyclopropylidene lithium carbenoids reacted with bis-(pinacolato)diboron in THF/Et2O at -110°C to give various 1,1-diborylated cyclopropanes in good yields. Treatment of the diborylated cyclopropanes with 3-chloro-1-lithio-3-methyl-1-butyne pro
