Literature DB >> 12785825

The first conjugate addition reaction of terminal alkynes catalytic in copper: conjugate addition of alkynes in water.

Thomas F Knöpfel1, Erick M Carreira.   

Abstract

We document that alkynyl copper reagents generated under aqueous conditions from terminal acetylenes, catalytic Cu(OAc)2, and sodium ascorbate undergo additions to Meldrum's acid-derived Michael acceptors at room temperature (Scheme 1). The additions are not only novel, but also constitute the first example of the conjugate addition reaction of an acetylide catalytic in copper.

Entities:  

Year:  2003        PMID： 12785825     DOI： 10.1021/ja035311z

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


  8 in total

Review 1.  Detection of electrophile-sensitive proteins.

Authors:  Stephanie B Wall; M Ryan Smith; Karina Ricart; Fen Zhou; Praveen K Vayalil; Joo-Yeun Oh; Aimee Landar
Journal:  Biochim Biophys Acta       Date:  2013-09-08

2.  Cu(II)-catalyzed aerobic hydroperoxidation of Meldrum's acid derivatives and application in intramolecular oxidation: a conceptual blueprint for O2/H2 dihydroxylation.

Authors:  Scott W Krabbe; Dung T Do; Jeffrey S Johnson
Journal:  Org Lett       Date:  2012-11-19       Impact factor: 6.005

3.  Scalable C-H Oxidation with Copper: Synthesis of Polyoxypregnanes.

Authors:  Yi Yang See; Aaron T Herrmann; Yoshinori Aihara; Phil S Baran
Journal:  J Am Chem Soc       Date:  2015-10-21       Impact factor: 15.419

4.  Infrared spectroscopic investigations on the metallation of terminal alkynes by Zn(OTf)2.

Authors:  Roger Fässler; Craig S Tomooka; Doug E Frantz; Erick M Carreira
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

5.  Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization.

Authors:  Miriam L O'Duill; Rei Matsuura; Yanyan Wang; Joshua L Turnbull; John A Gurak; De-Wei Gao; Gang Lu; Peng Liu; Keary M Engle
Journal:  J Am Chem Soc       Date:  2017-10-26       Impact factor: 15.419

6.  C-C bond formation via copper-catalyzed conjugate addition reactions to enones in water at room temperature.

Authors:  Bruce H Lipshutz; Shenlin Huang; Wendy Wen Yi Leong; Guofu Zhong; Nicholas A Isley
Journal:  J Am Chem Soc       Date:  2012-11-28       Impact factor: 15.419

Review 7.  Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams.

Authors:  Katherine M Byrd
Journal:  Beilstein J Org Chem       Date:  2015-04-23       Impact factor: 2.883

8.  Asymmetric synthesis of chiral β-alkynyl carbonyl and sulfonyl derivatives via sequential palladium and copper catalysis.

Authors:  Barry M Trost; James T Masters; Benjamin R Taft; Jean-Philip Lumb
Journal:  Chem Sci       Date:  2016-06-10       Impact factor: 9.825
  8 in total

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