English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
  Iron- or Palladium-Catalyzed Reaction Cascades Merging Cycloisomerization and Cross-Coupling Chemistry

Gomes, F., Echeverria, P.-G., & Fürstner, A. (2018). Iron- or Palladium-Catalyzed Reaction Cascades Merging Cycloisomerization and Cross-Coupling Chemistry. Chemistry – A European Journal, 24(63), 16814-16822. doi:10.1002/chem.201803360.

Item is

Basic

show hide
Genre: Journal Article

Files

show Files
hide Files
:
[381]SI.pdf (Supplementary material), 7MB
Name:
[381]SI.pdf
Description:
Supporting Information
OA-Status:
Visibility:
Public
MIME-Type / Checksum:
application/pdf / [MD5]
Technical Metadata:
Copyright Date:
-
Copyright Info:
-
License:
-

Locators

show

Creators

show
hide
 Creators:
Gomes, Filipe1, Author           
Echeverria, Pierre-Georges1, Author           
Fürstner, Alois1, Author           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

Content

show
hide
Free keywords: 1,3-dienes; cross-coupling reactions; iron catalysis; metallacycles; palladium
 Abstract: A conceptually novel reaction cascade is presented, which allows readily available enynes to be converted into functionalized 1,3‐dienes comprising a stereodefined tetrasubstituted alkene unit; such compounds are difficult to make by conventional means. The overall transformation is thought to commence with formation of a metallacyclic intermediate that evolves via cleavage of an unstrained C−X bond in its backbone. This non‐canonical cycloisomerization process is followed by a cross‐coupling step, such that reductive C−C bond formation regenerates the necessary low‐valent metal fragment and hence closes an intricate catalytic cycle. The cascade entails the formation of two new C−C bonds at the expense of the constitutional C−X entity of the substrate: importantly, the extruded group X must not be a heteroelement (X=O, NR), since activated β‐C−C bonds can also be broken. This concern was reduced to practice in two largely complementary formats: one procedure relies on the use of alkyl‐Grignard reagents in combination with catalytic amounts of Fe(acac)3, whereas the second method amalgamates cycloisomerization with Suzuki coupling by recourse to arylboronic acids and phosphine‐ligated palladium catalysts.

Details

show
hide
Language(s): eng - English
 Dates: 2018-07-022018-09-052018-11-15
 Publication Status: Published online
 Pages: 9
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/chem.201803360
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 24 (63) Sequence Number: - Start / End Page: 16814 - 16822 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058