Literature DB >> 20359187

Highly selective hydroiodation of alkynes using an iodine-hydrophosphine binary system.

Shin-ichi Kawaguchi1, Akiya Ogawa.   

Abstract

A novel hydroiodation of alkynes (1) using an iodine/hydrophosphine binary system takes place regioselectively to provide the corresponding Markovnikov-type adducts (2) in good yield. This hydroiodation is advantageous in terms of mild conditions, convenient operation, and tolerance to various functional groups.

Entities:  

Year:  2010        PMID： 20359187     DOI： 10.1021/ol1005246

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


  7 in total

1.  Formation of vinyl-, vinylhalide- or acyl-substituted quaternary carbon stereogenic centers through NHC-Cu-catalyzed enantioselective conjugate additions of Si-containing vinylaluminums to β-substituted cyclic enones.

Authors:  Tricia L May; Jennifer A Dabrowski; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2010-12-20       Impact factor: 15.419

2.  Regiospecific, enantiospecific total synthesis of C-19 methyl substituted sarpagine alkaloids dihydroperaksine-17-al and dihydroperaksine.

Authors:  Rahul V Edwankar; Chitra R Edwankar; Jeffrey Deschamps; James M Cook
Journal:  Org Lett       Date:  2011-08-30       Impact factor: 6.005

3.  Alpha-selective Ni-catalyzed hydroalumination of aryl- and alkyl-substituted terminal alkynes: practical syntheses of internal vinyl aluminums, halides, or boronates.

Authors:  Fang Gao; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

4.  Studies for the total synthesis of amphidinolide P.

Authors:  David R Williams; Brian J Myers; Liang Mi; Randall J Binder
Journal:  J Org Chem       Date:  2013-04-26       Impact factor: 4.354

5.  Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters.

Authors:  Weiye Guan; Alicia K Michael; Melissa L McIntosh; Liza Koren-Selfridge; John P Scott; Timothy B Clark
Journal:  J Org Chem       Date:  2014-07-14       Impact factor: 4.354

6.  General strategy for synthesis of C-19 methyl-substituted sarpagine/macroline/ajmaline indole alkaloids including total synthesis of 19(S),20(R)-dihydroperaksine, 19(S),20(R)-dihydroperaksine-17-al, and peraksine.

Authors:  Rahul V Edwankar; Chitra R Edwankar; Jeffrey R Deschamps; James M Cook
Journal:  J Org Chem       Date:  2014-10-15       Impact factor: 4.354

Review 7.  Metal-Mediated Halogen Exchange in Aryl and Vinyl Halides: A Review.

Authors:  Gwilherm Evano; Antoine Nitelet; Pierre Thilmany; Damien F Dewez
Journal:  Front Chem       Date:  2018-04-26       Impact factor: 5.221
  7 in total

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