English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
 
 
DownloadE-Mail
  Modular Synthesis of Furans with up to Four Different Substituents by a trans‐Carboboration Strategy

Jin, H., & Fürstner, A. (2020). Modular Synthesis of Furans with up to Four Different Substituents by a trans‐Carboboration Strategy. Angewandte Chemie International Edition, 59(32), 13618-13622. doi:10.1002/anie.202005560.

Item is

Files

show Files
hide Files
:
anie202005560-s1-supporting_information_v2_revised.pdf (Supplementary material), 9MB
Name:
anie202005560-s1-supporting_information_v2_revised.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:
Jin, Hongming1, Author           
Fürstner, Alois1, Author           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

Content

show
hide
Free keywords: carboboration; cascade reactions; cross-coupling; furans; trans-addition
 Abstract: Propargyl alcohols, on treatment with MHMDS (M = Na, K), B2(pin)2, an acid chloride and a palladium/copper co‐catalyst system, undergo a reaction cascade comprised of trans‐diboration, regioselective acylation, cyclization and dehydration to give trisubstituted furylboronic acid pinacol ester derivatives in good yields; subsequent Suzuki coupling allows a fourth substituent of choice to be introduced and hence tetrasubstituted (arylated) furans to be formed. In terms of modularity, the method seems unrivaled, not least because each product can be attained by two orthogonal but convergent ways (“diagonal split”). This asset is illustrated by the “serial” formation of a “library” of all twelve possible furan isomers that result from systematic permutation of four different substituents about the heterocyclic core.

Details

show
hide
Language(s): eng - English
 Dates: 2020-04-162020-05-062020-05-062020-08-03
 Publication Status: Issued
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202005560
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 59 (32) Sequence Number: - Start / End Page: 13618 - 13622 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851