Link to the University of Pittsburgh Homepage
Link to the University Library System Homepage Link to the Contact Us Form

A new regioselective Heck vinylation with enamides. Synthesis and investigation of fluorous-tagged bidentate ligands for fast separation

Vallin, KSA and Zhang, Q and Larhed, M and Curran, DP and Hallberg, A (2003) A new regioselective Heck vinylation with enamides. Synthesis and investigation of fluorous-tagged bidentate ligands for fast separation. Journal of Organic Chemistry, 68 (17). 6639 - 6645. ISSN 0022-3263

[img] Plain Text (licence)
Available under License : See the attached license file.

Download (1kB)

Abstract

Internal ligand-controlled Heck vinylations of enamides were performed with high regioselectivity and delivered moderate to good yields of dienamides. Controlled heating by microwave irradiation accelerated the palladium-catalyzed reactions, and full conversions were achieved after reaction times of only 15-30 min. New bidentate fluorous-tagged 1,3-bis(diphenylphosphino)propane ligands (F-dppp's) were synthesized and examined. The cationic vinylations of the enamides with F-dppp ligands rendered essentially the same α-selectivity and catalytic activity as in those vinylations where nonfluorous ligands were employed. After reaction, the fluorous-tagged ligand material was easily removed by convenient solid fluorous phase separation. The high selectivity, simplicity, and generality of the experimental procedure should make this approach to 2-acylamino-1,3-butadienes attractive.


Share

Citation/Export:
Social Networking:
Share |

Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Vallin, KSA
Zhang, Q
Larhed, M
Curran, DPcurran@pitt.eduCURRAN
Hallberg, A
Date: 1 September 2003
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 68
Number: 17
Page Range: 6639 - 6645
DOI or Unique Handle: 10.1021/jo034265i
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
PubMed ID: 12919028
Date Deposited: 07 Feb 2014 00:01
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/20459

Metrics

Monthly Views for the past 3 years

Plum Analytics

Altmetric.com


Actions (login required)

View Item View Item