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Literature DB >> 19122872

Bi(OTf)(3)-Catalyzed 5-Exo-Trig Cyclization via Halide Activation.

Abstract

Lewis acid activation of allyl halides utilizing Bi(OTf)(3) resulted in cationic cyclization of alkenes with high efficiency. While other Lewis acids could catalyzed this process with highly substituted alkenes, bismuth salts demonstrated unique reactivity in come cases. This suggested that bismuth triflate possesses intersting halophilic properties.

Entities: Chemical Gene

Year: 2008 PMID： 19122872 PMCID： PMC2516941 DOI： 10.1016/j.tetlet.2008.04.067

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

8 in total

Review 1. Formation and stability of carbocations and carbanions in water and intrinsic barriers to their reactions.

Authors: J P Richard; T L Amyes; M M Toteva
Journal: Acc Chem Res Date: 2001-12 Impact factor: 22.384

2. Metal-mediated reductive hydrodehalogenation of organic halides.

Authors: Francisco Alonso; Irina P Beletskaya; Miguel Yus
Journal: Chem Rev Date: 2002-11 Impact factor: 60.622

3. Superelectrophilic solvation.

Authors: George A Olah; Douglas A Klumpp
Journal: Acc Chem Res Date: 2004-04 Impact factor: 22.384

4. Activation of hydrogen- and halogen-bonding interactions in tetrathiafulvalene-based crystalline molecular conductors.

Authors: Marc Fourmigué; Patrick Batail
Journal: Chem Rev Date: 2004-11 Impact factor: 60.622

5. BiBr3-initiated tandem addition/silyl-Prins reactions to 2,6-disubstituted dihydropyrans.

Authors: Yajing Lian; Robert J Hinkle
Journal: J Org Chem Date: 2006-09-01 Impact factor: 4.354

6. Atom transfer cyclization catalyzed by InCl3 via halogen activation.

Authors: Gregory R Cook; Ryuji Hayashi
Journal: Org Lett Date: 2006-03-16 Impact factor: 6.005

7. Superacids.

Authors: G A Olah; G K Prakash; J Sommer
Journal: Science Date: 1979-10-05 Impact factor: 47.728

8. Remarkably mild and efficient intramolecular Friedel-Crafts cyclization catalyzed by In(III).

Authors: Ryuji Hayashi; Gregory R Cook
Journal: Org Lett Date: 2007-03-09 Impact factor: 6.005

8 in total

4 in total

1. Bi(OTf)3-, TfOH-, and TMSOTf-mediated, one-pot epoxide rearrangement, addition, and intramolecular silyl-modified Sakurai (ISMS) cascade toward dihydropyrans: comparison of catalysts and role of Bi(OTf)3.

Authors: R Frederick Lambert; Robert J Hinkle; Stephen E Ammann; Yajing Lian; Jia Liu; Shane E Lewis; Robert D Pike
Journal: J Org Chem Date: 2011-10-25 Impact factor: 4.354