Literature DB >> 16448133

Bismuth-catalyzed intermolecular hydroamination of 1,3-dienes with carbamates, sulfonamides, and carboxamides.

Hongbo Qin1, Noriyuki Yamagiwa, Shigeki Matsunaga, Masakatsu Shibasaki.   

Abstract

A Bi(OTf)(3)/Cu(CH(3)CN)(4)PF(6) system efficiently promoted intermolecular 1:1 hydroamination of 1,3-dienes with various carbamates, sulfonamides, and carboxamides to afford allylic amines in good yield (up to 96%). Reaction proceeded with 0.5-10 mol % catalyst loading at 25-100 degrees C (generally at 50 degrees C) in 1,4-dioxane within 24 h. The Bi(OTf)(3)/Cu(CH(3)CN)(4)PF(6) system constitutes a new entry into series of intermolecular hydroamination catalysis. Mechanistic studies and the postulated reaction mechanism are also discussed.

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Year:  2006        PMID: 16448133     DOI: 10.1021/ja056112d

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  8 in total

1.  Catalytic intermolecular hydroamination of vinyl ethers.

Authors:  Nirmal K Pahadi; Jon A Tunge
Journal:  Synlett       Date:  2009-12-01       Impact factor: 2.454

2.  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

3.  Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes.

Authors:  Xiao-Hui Yang; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-01-27       Impact factor: 15.419

4.  Synthesis of 2,6-disubstituted dihydropyrans via an efficient BiBr(3)-initiated three component, one-pot cascade.

Authors:  Robert J Hinkle; Yajing Lian; Lee C Speight; Heather E Stevenson; Melissa M Sprachman; Lauren A Katkish; M Christa Mattern
Journal:  Tetrahedron       Date:  2009-08-22       Impact factor: 2.457

5.  Intermolecular hydroamination of allenes with N-unsubstituted carbamates catalyzed by a gold(I) N-heterocyclic carbene complex.

Authors:  Robert E Kinder; Zhibin Zhang; Ross A Widenhoefer
Journal:  Org Lett       Date:  2008-06-21       Impact factor: 6.005

6.  Molecular Bismuth Cations: Assessment of Soft Lewis Acidity.

Authors:  Jacqueline Ramler; Crispin Lichtenberg
Journal:  Chemistry       Date:  2020-07-28       Impact factor: 5.236

7.  Two Faces of the Bi-O Bond: Photochemically and Thermally Induced Dehydrocoupling for Si-O Bond Formation.

Authors:  Jacqueline Ramler; Johannes Schwarzmann; Andreas Stoy; Crispin Lichtenberg
Journal:  Eur J Inorg Chem       Date:  2021-12-18       Impact factor: 2.551

8.  Bismuth Subnitrate-Catalyzed Markovnikov-Type Alkyne Hydrations under Batch and Continuous Flow Conditions.

Authors:  Zsanett Szécsényi; Ferenc Fülöp; Sándor B Ötvös
Journal:  Molecules       Date:  2021-05-12       Impact factor: 4.411

  8 in total

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