eprintid: 20459
rev_number: 16
userid: 1418
dir: disk0/00/02/04/59
datestamp: 2014-02-07 00:01:04
lastmod: 2019-02-02 15:58:40
status_changed: 2014-02-07 00:01:04
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Vallin, KSA
creators_name: Zhang, Q
creators_name: Larhed, M
creators_name: Curran, DP
creators_name: Hallberg, A
creators_email: 
creators_email: 
creators_email: 
creators_email: curran@pitt.edu
creators_email: 
creators_id: 
creators_id: 
creators_id: 
creators_id: CURRAN
creators_id: 
title: A new regioselective Heck vinylation with enamides. Synthesis and investigation of fluorous-tagged bidentate ligands for fast separation
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
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.
date: 2003-09-01
date_type: published
publication: Journal of Organic Chemistry
volume: 68
number: 17
pagerange: 6639 - 6645
refereed: TRUE
issn: 0022-3263
id_number: 10.1021/jo034265i
pmid: 12919028
citation:   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     
document_url: http://d-scholarship-dev.library.pitt.edu/20459/1/licence.txt