Literature DB >> 15128243

Formation of 3-halobenzyne: solvent effects and cycloaddition adducts.

Jotham W Coe1, Michael C Wirtz, Crystal G Bashore, John Candler.   

Abstract

Noncoordinating solvents permit the halogen-metal exchange-induced formation of benzyne (aryne) from di- and trihalobenzene precursors in the presence of cyclopentadiene to give 1,4-dihydro-1,4-methano-naphthalenes. Studies with mixed halide precursors and nonacidic Diels-Alder diene traps reveal that ethereal and hydrocarbon solvents influence the halide leaving group facility, resulting in a reversal of 3-halobenzyne regioselectivity.

Entities:  

Year:  2004        PMID： 15128243     DOI： 10.1021/ol049655l

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  New synthesis of (±)-cis-trikentrin A via tandem indole aryne cycloaddition/Negishi reaction. Applications to library development.

Authors:  Neil Brown; Diheng Luo; Joseph A Decapo; Keith R Buszek
Journal:  Tetrahedron Lett       Date:  2009-12-23       Impact factor: 2.415

2.  Regioselective Diels-Alder cycloadditions and other reactions of 4,5-, 5,6-, and 6,7-indole arynes.

Authors:  Neil Brown; Diheng Luo; David Vandervelde; Shaorong Yang; Allen Brassfield; Keith R Buszek
Journal:  Tetrahedron Lett       Date:  2009-01-07       Impact factor: 2.415

3.  Concise total synthesis of (+/-)-cis-trikentrin A and (+/-)-herbindole A via intermolecular indole aryne cycloaddition.

Authors:  Keith R Buszek; Neil Brown; Diheng Luo
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005
  3 in total

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