Tetrahedron letters

Electrophilic allylation of arenes with in situ generated allyltriarylbismuthonium compound: The bismuth-mediated polarity inversion of allylsilanes

Y Matano, M Yoshimune, H Suzuki

Index: Matano, Yoshihiro; Yoshimune, Masanori; Suzuki, Hitomi Tetrahedron Letters, 1995 , vol. 36, # 41 p. 7475 - 7478

Full Text: HTML

Citation Number: 16

Abstract

Reaction of triarylbismuth difluorides 1 with allyltrimethylsilane 2 in CH2Cl2 in the presence of BF3· OEt2 at low temperature generates allyltriarylbismuthonium compound 3 as a pale yellow solution, in which aromatic hydrocarbons and ethers, triphenylphosphine, dimethyl sulfide, p-toluenesulfinate, and thiophenol are all readily allylated to afford the corresponding allyl derivatives in moderate to good yields.

Related Articles:

Vanadium-catalyzed enantioselective oxidation of allyl sulfides

[Zeng, Qingle; Gao, Yuxing; Dong, Junyu; Weng, Wen; Zhao, Yufen Tetrahedron Asymmetry, 2011 , vol. 22, # 7 p. 717 - 721]

Bi or Cd-Induced Coupling of Sulfonyl Chlorides with Allylic Halides. A Simple Synthesis of Allylic Sulfones

[Baruah, Mukulesh; Boruah, Anima; Prajapati, Dipak; Sandhu, Jagir S. Synlett, 1998 , # 10 p. 1083 - 1084]

Ether aryl sulfonic acid esters with improved antimalarial/anticancer activities

[Betts, Lynn M.; Tam, Nga Chiu; Kabir, S. M. Humayun; Langler, Richard F.; Crandall, Ian Australian Journal of Chemistry, 2006 , vol. 59, # 4 p. 277 - 282]

Bi or Cd-Induced Coupling of Sulfonyl Chlorides with Allylic Halides. A Simple Synthesis of Allylic Sulfones

[Baruah, Mukulesh; Boruah, Anima; Prajapati, Dipak; Sandhu, Jagir S. Synlett, 1998 , # 10 p. 1083 - 1084]

Sulfonylation of organometallic reagents with arenesulfonyl fluorides: a simple one-step synthesis of sulfones

[Frye, Leah L.; Sullivan, Eileen L.; Cusack, Kevin P.; Funaro, John M. Journal of Organic Chemistry, 1992 , vol. 57, # 2 p. 697 - 701]

More Articles...