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Palladium(0)-catalyzed intramolecular [2+2+2] alkyne cyclotrimerizations with electron-deficient diynes and triynes.

In the presence of 2.5 mol % of [Pd(dba)] (dba=dibenzylideneacetone) and 5 mol % of PPh, nearly equimolar amounts of dimethyl nona‐2,7‐diyne‐1,9‐dioate derivatives (diyne diesters) and dialkyl acetylenedicarboxylates were allowed to react in toluene at 110 °C to afford [2+2+2] cycloadducts in modera... Full description

Journal Title: Chemistry (Weinheim an der Bergstrasse Germany), June 6, 2003, Vol.9(11), pp.2469-2483
Main Author: Yamamoto, Yoshihiko
Other Authors: Nagata, Asako , Nagata, Hitomi , Ando, Yoji , Arikawa, Yasuhiro , Tatsumi, Kazuyuki , Itoh, Kenji
Format: Electronic Article Electronic Article
Language: English
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ID: ISSN: 0947-6539
Link: http://search.proquest.com/docview/73336115/?pq-origsite=primo
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title: Palladium(0)-catalyzed intramolecular [2+2+2] alkyne cyclotrimerizations with electron-deficient diynes and triynes.
format: Article
creator:
  • Yamamoto, Yoshihiko
  • Nagata, Asako
  • Nagata, Hitomi
  • Ando, Yoji
  • Arikawa, Yasuhiro
  • Tatsumi, Kazuyuki
  • Itoh, Kenji
subjects:
  • Alkynes
  • Cyclotrimerization
  • Homogeneous Catalysis
  • Metallacycles
  • Palladium
ispartof: Chemistry (Weinheim an der Bergstrasse, Germany), June 6, 2003, Vol.9(11), pp.2469-2483
description: In the presence of 2.5 mol % of [Pd(dba)] (dba=dibenzylideneacetone) and 5 mol % of PPh, nearly equimolar amounts of dimethyl nona‐2,7‐diyne‐1,9‐dioate derivatives (diyne diesters) and dialkyl acetylenedicarboxylates were allowed to react in toluene at 110 °C to afford [2+2+2] cycloadducts in moderate‐to‐good yields. Similarly, dimethyl trideca‐2,7,12‐triyne‐1,13‐dioate derivatives (triyne diesters) were catalytically transformed into phthalic acid ester analogues in excellent yields. To gain insight into the mechanism of these intramolecular alkyne cyclotrimerizations, stoichiometric reactions of [Pd(dba)] with a diyne diester and a triyne diester bearing ether tethers were conducted in acetone at room temperature to furnish an oligomeric bicyclopalladacyclopentadiene and a Pd triyne complex, respectively. The structures of these novel complexes were unequivocally determined by Xray structure analysis. The isolated triyne complex was heated at 50 °C or treated with PPh in acetone at room temperature to afford the arene product. Furthermore, the same complex catalyzed the triyne cyclization with or without PPh. , such as diyne diesters, acetylenedicarboxylic acid esters, and triyne diesters undergo palladium()‐catalyzed intramolecular [2+2+2] alkyne cyclotrimerizations in good yields (see scheme). Relevant intermediates, bicyclic palladacyclopentadiene, and Pd triyne complexes, were synthesized and unequivocally characterized by single‐crystal Xray analyses.
language: eng
source:
identifier: ISSN: 0947-6539
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
url: Link


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titlePalladium(0)-catalyzed intramolecular [2+2+2] alkyne cyclotrimerizations with electron-deficient diynes and triynes.
creatorYamamoto, Yoshihiko ; Nagata, Asako ; Nagata, Hitomi ; Ando, Yoji ; Arikawa, Yasuhiro ; Tatsumi, Kazuyuki ; Itoh, Kenji
contributorYamamoto, Yoshihiko (correspondence author) ; Yamamoto, Yoshihiko (record owner)
ispartofChemistry (Weinheim an der Bergstrasse, Germany), June 6, 2003, Vol.9(11), pp.2469-2483
identifierISSN: 0947-6539
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subjectAlkynes ; Cyclotrimerization ; Homogeneous Catalysis ; Metallacycles ; Palladium;
descriptionIn the presence of 2.5 mol % of [Pd(dba)] (dba=dibenzylideneacetone) and 5 mol % of PPh, nearly equimolar amounts of dimethyl nona‐2,7‐diyne‐1,9‐dioate derivatives (diyne diesters) and dialkyl acetylenedicarboxylates were allowed to react in toluene at 110 °C to afford [2+2+2] cycloadducts in moderate‐to‐good yields. Similarly, dimethyl trideca‐2,7,12‐triyne‐1,13‐dioate derivatives (triyne diesters) were catalytically transformed into phthalic acid ester analogues in excellent yields. To gain insight into the mechanism of these intramolecular alkyne cyclotrimerizations, stoichiometric reactions of [Pd(dba)] with a diyne diester and a triyne diester bearing ether tethers were conducted in acetone at room temperature to furnish an oligomeric bicyclopalladacyclopentadiene and a Pd triyne complex, respectively. The structures of these novel complexes were unequivocally determined by Xray structure analysis. The isolated triyne complex was heated at 50 °C or treated with PPh in acetone at room temperature to afford the arene product. Furthermore, the same complex catalyzed the triyne cyclization with or without PPh. , such as diyne diesters, acetylenedicarboxylic acid esters, and triyne diesters undergo palladium()‐catalyzed intramolecular [2+2+2] alkyne cyclotrimerizations in good yields (see scheme). Relevant intermediates, bicyclic palladacyclopentadiene, and Pd triyne complexes, were synthesized and unequivocally characterized by single‐crystal Xray analyses.
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