1352656-46-2Relevant academic research and scientific papers
Enantiospecific, nickel-catalyzed cross-couplings of allylic pivalates and arylboroxines
Srinivas, Harathi D.,Zhou, Qi,Watson, Mary P.
supporting information, p. 3596 - 3599 (2014/07/21)
We have developed an enantiospecific, nickel-catalyzed cross-coupling of unsymmetric 1,3-disubstituted allylic pivalates with arylboroxines. The success of this reaction relies on the use of BnPPh2 as a supporting ligand for the nickel(0) catalyst and NaOMe as a base. This method shows excellent functional group tolerance and broad scope in both the allylic pivalate and arylboroxine, enabling the preparation of 1,3-diaryl allylic products in high yields with excellent levels of regioselectivity and stereochemical fidelity.
Palladium-catalyzed stereospecific cross-coupling of enantioenriched allylic alcohols with boronic acids
Wu, Hai-Bian,Ma, Xian-Tao,Tian, Shi-Kai
supporting information, p. 219 - 221 (2014/01/06)
In the presence of 2.5 mol% Pd2(dba)3-TMEDA (1 : 4), a range of enantioenriched allylic alcohols smoothly coupled with boronic acids in a highly regioselective fashion with inversion of configuration to afford structurally diverse alkenes in good yields with perfect retention of ee.
Nickel-catalyzed reductive allylation of aryl bromides with allylic acetates
Cui, Xiaozhan,Wang, Shulin,Zhang, Yuwei,Deng, Wei,Qian, Qun,Gong, Hegui
supporting information, p. 3094 - 3097 (2013/05/23)
This paper highlights Ni-catalyzed allylation of electron-rich aryl bromides with a variety of substituted allylic carbonates using zinc as the terminal reductant, affording E-alkenes regioselectively in good to excellent yields by the addition of aryl to the less hindered allylic carbon. The electron-deficient aryl bromides and chlorides are also highly efficient coupling partners. The Royal Society of Chemistry 2013.
Pd-catalyzed regioselective and stereospecific Suzuki-Miyaura coupling of allylic carbonates with arylboronic acids
Li, Chenguang,Xing, Juxiang,Zhao, Jingming,Huynh, Patrick,Zhang, Wanbin,Jiang, Pingkai,Zhang, Yong Jian
supporting information; experimental part, p. 390 - 393 (2012/02/15)
The Pd-catalyzed Suzuki-Miyaura coupling reaction of unsymmetric 1,3-disubstituted secondary allylic carbonates with arylboronic acids has been developed in a wet solvent under a base-free system to afford allyl-aryl coupling products in a high level of isolated yields with complete regio- and E/Z-selectivities with good to excellent chemoselectivities. The coupling reaction of optically active allyl carbonates gave allyl-aryl coupling products with excellent enantioselectivities with inversion of the stereochemistry. This coupling method was successfully applied to the synthesis of (S)-naproxen.
