Literature DB >> 19779575

Coupling Pd-Catalyzed Alcohol Oxidation to Olefin Functionalization: Hydrohalogenation/Hydroalkoxylation of Styrenes.

Susanne M Podhajsky1, Matthew S Sigman.   

Abstract

A hydrochlorination reaction of styrenes catalyzed by Pd(II) in combination with Cu(II) was developed, which was followed by an in situ conversion of electron-rich products to an ether in the presence of an alcohol. Mechanistic experiments indicate that olefin functionalization is coupled to an alcohol oxidation, wherein a Pd hydride formed in the β-hydride elimination step of the alcohol oxidation was incorporated into the product.

Entities:  

Year:  2007        PMID： 19779575      PMCID： PMC2749245          DOI： 10.1021/om700675z

Source DB:  PubMed          Journal:  Organometallics        ISSN： 0276-7333            Impact factor:   3.876


  23 in total

1.  Palladium-catalyzed equilibrium addition of acidic OH groups across dienes.

Authors:  Masaru Utsunomiya; Motoi Kawatsura; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2003       Impact factor: 15.336

2.  Gold(I)-catalyzed intermolecular addition of phenols and carboxylic acids to olefins.

Authors:  Cai-Guang Yang; Chuan He
Journal:  J Am Chem Soc       Date:  2005-05-18       Impact factor: 15.419

3.  The changing faces of halogenated marine natural products: total synthesis of the reported structures of elatenyne and an enyne from Laurencia majuscula.

Authors:  Helen M Sheldrake; Craig Jamieson; Jonathan W Burton
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-06       Impact factor: 15.336

4.  A simple catalytic method for the regioselective halogenation of arenes.

Authors:  Dipannita Kalyani; Allison R Dick; Waseem Q Anani; Melanie S Sanford
Journal:  Org Lett       Date:  2006-06-08       Impact factor: 6.005

5.  Palladium(II)-catalyzed aerobic hydroalkoxylation of styrenes containing a phenol.

Authors:  Keith M Gligorich; Mitchell J Schultz; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

6.  Catalytic formation of C-O bonds by alkene activation: Lewis acid-cycloisomerisation of olefinic alcohols.

Authors:  Lydie Coulombel; Isabelle Favier; Elisabet Duñach
Journal:  Chem Commun (Camb)       Date:  2005-03-09       Impact factor: 6.222

7.  Origin of enantioselection in chiral alcohol oxidation catalyzed by Pd[(-)-sparteine]Cl2.

Authors:  Jaime A Mueller; Anne Cowell; Bert D Chandler; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2005-10-26       Impact factor: 15.419

8.  Ruthenium catalyzed addition reaction of carboxylic acid across olefins without beta-hydride elimination.

Authors:  Yohei Oe; Tetsuo Ohta; Yoshihiko Ito
Journal:  Chem Commun (Camb)       Date:  2004-06-15       Impact factor: 6.222

9.  Ligand-modulated palladium-catalyzed aerobic alcohol oxidations.

Authors:  Matthew S Sigman; David R Jensen
Journal:  Acc Chem Res       Date:  2006-03       Impact factor: 22.384

10.  Pd(II)-catalyzed conversion of styrene derivatives to acetals: impact of (-)-sparteine on regioselectivity.

Authors:  Amy M Balija; Kara J Stowers; Mitchell J Schultz; Matthew S Sigman
Journal:  Org Lett       Date:  2006-03-16       Impact factor: 6.005
View more
  11 in total

1.  Intercepting Wacker intermediates with arenes: C-H functionalization and dearomatization.

Authors:  Bryan S Matsuura; Allison G Condie; Ian A McBee; Ryan C Buff; Gregory J Karahalis; Corey R J Stephenson
Journal:  Org Lett       Date:  2011-11-09       Impact factor: 6.005

2.  Pd(II)-catalyzed oxidative 1,1-diarylation of terminal olefins.

Authors:  Erik W Werner; Kaveri B Urkalan; Matthew S Sigman
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

3.  Asymmetric palladium-catalyzed hydroarylation of styrenes and dienes.

Authors:  Susanne M Podhajsky; Yasumasa Iwai; Amanda Cook-Sneathen; Matthew S Sigman
Journal:  Tetrahedron       Date:  2011-06-17       Impact factor: 2.457

4.  Recent advancements and challenges of palladium(II)-catalyzed oxidation reactions with molecular oxygen as the sole oxidant.

Authors:  Keith M Gligorich; Matthew S Sigman
Journal:  Chem Commun (Camb)       Date:  2009-05-14       Impact factor: 6.222

5.  Palladium-catalyzed hydroalkylation of styrenes with organozinc reagents to form carbon-carbon sp3-sp3 bonds under oxidative conditions.

Authors:  Kaveri Balan Urkalan; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2009-12-23       Impact factor: 15.419

6.  HBr-DMPU: The First Aprotic Organic Solution of Hydrogen Bromide.

Authors:  Zhou Li; Rene Ebule; Jessica Kostyo; Gerald B Hammond; Bo Xu
Journal:  Chemistry       Date:  2017-08-16       Impact factor: 5.236

7.  Palladium-catalyzed oxidative intermolecular difunctionalization of terminal alkenes with organostannanes and molecular oxygen.

Authors:  Kaveri Balan Urkalan; Matthew S Sigman
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  A new approach to carbon-carbon bond formation: Development of aerobic Pd-catalyzed reductive coupling reactions of organometallic reagents and styrenes.

Authors:  Keith M Gligorich; Yasumasa Iwai; Sarah A Cummings; Matthew S Sigman
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

9.  Metal-free, Regio-, and Stereo-Controlled Hydrochlorination and Hydrobromination of Ynones and Ynamides.

Authors:  Xiaojun Zeng; Zhichao Lu; Shiwen Liu; Gerald B Hammond; Bo Xu
Journal:  J Org Chem       Date:  2017-12-07       Impact factor: 4.354

10.  Hydrogen-Bonding-Assisted Brønsted Acid and Gold Catalysis: Access to Both (E)- and (Z)-1,2-Haloalkenes via Hydrochlorination of Haloalkynes.

Authors:  Xiaojun Zeng; Shiwen Liu; Gerald B Hammond; Bo Xu
Journal:  ACS Catal       Date:  2017-12-15       Impact factor: 13.084
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.