Literature DB >> 15221826

Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: recent developments and trends.

Matthias Beller1, Jayasree Seayad, Annegret Tillack, Haijun Jiao.   

Abstract

The regioselective functionalization of terminal alkenes and alkynes is of utmost importance for the synthesis of a wide variety of organic products. Based on the original observation by Vladimir Markovnikov-the pioneer of this field of research-in the 19th century, the possible regioisomeric products are classified as Markovnikov or anti-Markovnikov products. Contrary to traditional belief, it is nowadays possible to control the regiochemistry of various additions of nucleophiles to alkenes and alkynes by applying different transition-metal catalysts. Recent developments in this area of selective functionalization of alkenes and alkynes are reviewed.

Entities:  

Year:  2004        PMID: 15221826     DOI: 10.1002/anie.200300616

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  60 in total

1.  Allylic C-H acetoxylation with a 4,5-diazafluorenone-ligated palladium catalyst: a ligand-based strategy to achieve aerobic catalytic turnover.

Authors:  Alison N Campbell; Paul B White; Ilia A Guzei; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2010-11-03       Impact factor: 15.419

2.  A stereoselective intramolecular halo-etherification of chiral enamides in the synthesis of halogenated cyclic ethers.

Authors:  Changhong Ko; Richard P Hsung; Ziyad F Al-Rashid; John B Feltenberger; Ting Lu; Jin-Haek Yang; Yonggang Wei; Craig A Zificsak
Journal:  Org Lett       Date:  2007-10-02       Impact factor: 6.005

3.  Direct, catalytic hydroaminoalkylation of unactivated olefins with N-alkyl arylamines.

Authors:  Seth B Herzon; John F Hartwig
Journal:  J Am Chem Soc       Date:  2007-05-03       Impact factor: 15.419

4.  Mild, rhodium-catalyzed intramolecular hydroamination of unactivated terminal and internal alkenes with primary and secondary amines.

Authors:  Zhijian Liu; John F Hartwig
Journal:  J Am Chem Soc       Date:  2008-01-10       Impact factor: 15.419

5.  Homogeneous catalytic hydroamination of alkynes and allenes with ammonia.

Authors:  Vincent Lavallo; Guido D Frey; Bruno Donnadieu; Michele Soleilhavoup; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Temporal separation of catalytic activities allows anti-Markovnikov reductive functionalization of terminal alkynes.

Authors:  Le Li; Seth B Herzon
Journal:  Nat Chem       Date:  2013-11-17       Impact factor: 24.427

7.  Hydrothiolation of benzyl mercaptan to arylacetylene: application to the synthesis of (E) and (Z)-isomers of ON 01910·Na (Rigosertib®), a phase III clinical stage anti-cancer agent.

Authors:  Venkat R Pallela; Muralidhar R Mallireddigari; Stephen C Cosenza; Balaiah Akula; D R C Venkata Subbaiah; E Premkumar Reddy; M V Ramana Reddy
Journal:  Org Biomol Chem       Date:  2013-02-06       Impact factor: 3.876

8.  Enzyme inhibition by hydroamination: design and mechanism of a hybrid carmaphycin-syringolin enone proteasome inhibitor.

Authors:  Daniela B B Trivella; Alban R Pereira; Martin L Stein; Yusuke Kasai; Tara Byrum; Frederick A Valeriote; Dean J Tantillo; Michael Groll; William H Gerwick; Bradley S Moore
Journal:  Chem Biol       Date:  2014-06-12

9.  Serendipitous discovery of the catalytic hydroammoniumation and methylamination of alkynes.

Authors:  Xiaoming Zeng; Rei Kinjo; Bruno Donnadieu; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

10.  Copper-catalyzed regioselective ortho C-H cyanation of vinylarenes.

Authors:  Yang Yang; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-06       Impact factor: 15.336

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