期刊文献+

Copper-catalyzed decarboxylative hydroboration of phenylpropiolic acids under ligand-free or both ligand-and base-free conditions 被引量:1

Copper-catalyzed decarboxylative hydroboration of phenylpropiolic acids under ligand-free or both ligand-and base-free conditions
原文传递
导出
摘要 An efficient copper-catalyzed decarboxylative hydroboration of phenylpropiolic acids with bis(pinacolato)diboron was developed, affording b-vinylboronates as the only products in high yields. Extra hydrogen sources such as methanol are not needed in this catalytic system. This reaction could be performed successfully under ligand- and base-free conditions. It demonstrated that phenylpropiolic acids can be employed as alkyne synthons in the hydroboration reaction and exhibited good reactivity and higher selectivity than terminal alkynes. An efficient copper-catalyzed decarboxylative hydroboration of phenylpropiolic acids with bis(pinacolato)diboron was developed, affording b-vinylboronates as the only products in high yields. Extra hydrogen sources such as methanol are not needed in this catalytic system. This reaction could be performed successfully under ligand- and base-free conditions. It demonstrated that phenylpropiolic acids can be employed as alkyne synthons in the hydroboration reaction and exhibited good reactivity and higher selectivity than terminal alkynes.
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2016年第4期571-574,共4页 中国化学快报(英文版)
基金 Financial support from the National Science Foundation of China (No. 21202049) the Recruitment Program of Global Experts (1000 Talents Plan) Fujian Hundred Talents Plan Program of Innovative Research Team of Huaqiao University Instrumental Analysis Center of Huaqiao University for analysis support
关键词 DECARBOXYLATION HYDROBORATION LIGAND-FREE Base-free Copper-catalysis Decarboxylation Hydroboration Ligand-free Base-free Copper-catalysis
  • 相关文献

参考文献32

  • 1B. Carboni, L. Monnier, Recent developments in the chemistry of amine- and phosphine-boranes, Tetrahedron 55 (1999) 1197-1248.
  • 2H.C. Brown, T. Hamaoka, N. Ravindran, Reaction of alkenylboronic acids with iodine under the influence of base. Simple procedure for the stereospecific conversion of terminal alkynes into trans-l-alkenyl iodides via hydroboration, J. Am. Chem. Soc. 95 (1973) 5786-5788.
  • 3G.A. Molander, N.M. Ellis, Highly stereoselective synthesis of cis-alkenyl pinacolboronates and potassium cis-alkenyltrifluoroborates via a hydrobora- tion/protodeboronation approach, J. Org. Chem. 73 (2008) 6841-6844.
  • 4R.E. Shade, A.M. Hyde, J.C. OIsen, C.A. Merlic, Copper-promoted coupling of vinyl boronates and alcohols: a mild synthesis of allyl vinyl ethers, J. Am. Chem. Soc. 132 (2010) 1202-1203.
  • 5P.J. Riss, S. Lu, S. Telu, F.L Aigbirhio, V.W. Pike, Cul-catalyzed 11C carboxylation of boronic acid esters: a rapid and convenient entry to 11C-labeled carboxylic acids, esters, and amides, Angew. Chem. Int. Ed. 51 (2012) 2698-2702.
  • 6N.R. Candelas, F. Montalbano, P.M.S.D. Cal, P.M.P. Gois, Boronic acids and esters in the Petasis-borono Mannich multicomponent reaction, Chem. Rev. 110 (2010) 6169-6193;.
  • 7M. Tredwell, S.M. Preshlock, N.J. Taylor, et al., A general copper-mediated nucleophilic 18F fluorination of arenes, Angew. Chem. Int. Ed. 53 (2014) 7751- 7755.
  • 8Y.D. Bidal, F. Lazreg, C.S.J. Cazin, Copper-catalyzed regioselective formation of Tri- and tetrasubstituted vinylboronates in air, ACS Catal. 4 (2014) 1564-1569.
  • 9C. Gunanathan, M. Holscher, F. Pan, W. Leitner, Ruthenium catalyzed hydro- boration of terminal alkyoes to Z-vinylboronates, J. Am. Chem. Soc. 134 (2012) 14349-14352.
  • 10K. Takahashi, T. lshiyama, N. Miyaura, A borylcopper species generated from bis(pinacolato)diboron and its additions to α,β-unsaturated carbonyl compounds and terminal alkynes, J. Organomet. Chem. 625 (2001) 4?-53.

引证文献1

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部