Literature DB >> 24980625

Palladium catalyzed intramolecular acylcyanation of alkenes using α-iminonitriles.

Naveen R Rondla1, Jodi M Ogilvie, Zhongda Pan, Christopher J Douglas.   

Abstract

Reported here is a palladium catalyzed intramolecular acylcyanation of alkenes using α-iminonitriles. Through this method, highly functionalized indanones are synthesized in moderate to high yields using Pd(PPh3)4, without need for any additional ligands, and a common Lewis acid (ZnCl2). Additionally, the reaction tolerates substitution at various positions on the aromatic ring including electron donating and electron withdrawing groups.

Entities:  

Mesh：

Substances：

Year:  2014        PMID： 24980625      PMCID： PMC4137412          DOI： 10.1039/c4cc04068f

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  19 in total

1.  Metal-catalysed cleavage of carbon-carbon bonds.

Authors:  Masahiro Murakami; Takanori Matsuda
Journal:  Chem Commun (Camb)       Date:  2010-10-18       Impact factor: 6.222

2.  Intramolecular arylcyanation of alkenes catalyzed by nickel/AlMe2Cl.

Authors:  Yoshiaki Nakao; Shiro Ebata; Akira Yada; Tamejiro Hiyama; Masashi Ikawa; Sensuke Ogoshi
Journal:  J Am Chem Soc       Date:  2008-09-06       Impact factor: 15.419

3.  Palladium-catalyzed cyanoesterification of norbornenes with cyanoformates via the NC-Pd-COOR (R = Me and Et) intermediate.

Authors:  Yasushi Nishihara; Yoshiaki Inoue; Masumi Itazaki; Kentaro Takagi
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

4.  Rate-limiting step of the Rh-catalyzed carboacylation of alkenes: C-C bond activation or migratory insertion?

Authors:  J Patrick Lutz; Colin M Rathbun; Susan M Stevenson; Breanna M Powell; Timothy S Boman; Casey E Baxter; John M Zona; Jeffrey B Johnson
Journal:  J Am Chem Soc       Date:  2011-12-20       Impact factor: 15.419

5.  Palladium-catalyzed C-CN activation for intramolecular cyanoesterification of alkynes.

Authors:  Naveen R Rondla; Samuel M Levi; Jonathan M Ryss; Rachel A Vanden Berg; Christopher J Douglas
Journal:  Org Lett       Date:  2011-03-21       Impact factor: 6.005

6.  Intramolecular aminocyanation of alkenes by N-CN bond cleavage.

Authors:  Zhongda Pan; Sarah M Pound; Naveen R Rondla; Christopher J Douglas
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-09       Impact factor: 15.336

7.  Intramolecular oxycyanation of alkenes by cooperative Pd/BPh3 catalysis.

Authors:  Dennis C Koester; Masato Kobayashi; Daniel B Werz; Yoshiaki Nakao
Journal:  J Am Chem Soc       Date:  2012-04-06       Impact factor: 15.419

8.  Nickel-catalyzed arylcyanation of alkynes.

Authors:  Yoshiaki Nakao; Shinichi Oda; Tamejiro Hiyama
Journal:  J Am Chem Soc       Date:  2004-11-03       Impact factor: 15.419

9.  Intramolecular aminocyanation of alkenes by cooperative palladium/boron catalysis.

Authors:  Yosuke Miyazaki; Naoki Ohta; Kazuhiko Semba; Yoshiaki Nakao
Journal:  J Am Chem Soc       Date:  2014-03-03       Impact factor: 15.419

10.  Catalytic carbon-carbon sigma bond activation: an intramolecular carbo-acylation reaction with acylquinolines.

Authors:  Ashley M Dreis; Christopher J Douglas
Journal:  J Am Chem Soc       Date:  2009-01-21       Impact factor: 15.419
View more
  2 in total

1.  Mechanistic Model for Enantioselective Intramolecular Alkene Cyanoamidation via Palladium-Catalyzed C-CN Bond Activation.

Authors:  Grant B Frost; Nicholas A Serratore; Jodi M Ogilvie; Christopher J Douglas
Journal:  J Org Chem       Date:  2017-03-15       Impact factor: 4.354

2.  "Cut and Sew" Transformations via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation.

Authors:  Peng-Hao Chen; Brent A Billett; Tatsuhiro Tsukamoto; Guangbin Dong
Journal:  ACS Catal       Date:  2017-01-06       Impact factor: 13.084
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.