Carbonyl Propargylation from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Enynes as Surrogates to Preformed Allenylmetal Reagents: A Ruthenium-Catalyzed C–C Bond-Forming Transfer Hydrogenation

RL Patman; VM Williams; JF Bower; MJ Krische

doi:10.1002/anie.200801359

Carbonyl Propargylation from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Enynes as Surrogates to Preformed Allenylmetal Reagents: A Ruthenium-Catalyzed C–C Bond-Forming Transfer Hydrogenation

RL Patman, VM Williams, JF Bower, MJ Krische

Research output: Contribution to journal › Article (Academic Journal) › peer-review

82 Citations (Scopus)

Abstract

Transcending oxidation level: Under the conditions of ruthenium-catalyzed transfer hydrogenation, conjugated enynes couple to benzylic, allylic, and aliphatic alcohols or aldehydes to furnish products of carbonyl propargylation (see scheme; dppf=1,1′-bis(diphenylphosphino)ferrocene, TBS=tert-butyldimethylsilyl). Isotopic labeling studies corroborate a mechanism involving hydrogen donation from the alcohol to the enyne.

Translated title of the contribution	Carbonyl Propargylation from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Enynes as Surrogates to Preformed Allenylmetal Reagents: A Ruthenium-Catalyzed C–C Bond-Forming Transfer Hydrogenation
Original language	English
Pages (from-to)	5220-5223
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	28
DOIs	https://doi.org/10.1002/anie.200801359
Publication status	Published - 2008

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title = "Carbonyl Propargylation from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Enynes as Surrogates to Preformed Allenylmetal Reagents: A Ruthenium-Catalyzed C–C Bond-Forming Transfer Hydrogenation",

abstract = "Transcending oxidation level: Under the conditions of ruthenium-catalyzed transfer hydrogenation, conjugated enynes couple to benzylic, allylic, and aliphatic alcohols or aldehydes to furnish products of carbonyl propargylation (see scheme; dppf=1,1′-bis(diphenylphosphino)ferrocene, TBS=tert-butyldimethylsilyl). Isotopic labeling studies corroborate a mechanism involving hydrogen donation from the alcohol to the enyne.",

author = "RL Patman and VM Williams and JF Bower and MJ Krische",

year = "2008",

doi = "10.1002/anie.200801359",

language = "English",

volume = "47",

pages = "5220--5223",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "Wiley-VCH Verlag",

number = "28",

}

Patman, RL, Williams, VM, Bower, JF & Krische, MJ 2008, 'Carbonyl Propargylation from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Enynes as Surrogates to Preformed Allenylmetal Reagents: A Ruthenium-Catalyzed C–C Bond-Forming Transfer Hydrogenation', Angewandte Chemie - International Edition, vol. 47, no. 28, pp. 5220-5223. https://doi.org/10.1002/anie.200801359

Carbonyl Propargylation from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Enynes as Surrogates to Preformed Allenylmetal Reagents : A Ruthenium-Catalyzed C–C Bond-Forming Transfer Hydrogenation. / Patman, RL; Williams, VM; Bower, JF et al.

In: Angewandte Chemie - International Edition, Vol. 47, No. 28, 2008, p. 5220-5223.

Research output: Contribution to journal › Article (Academic Journal) › peer-review

TY - JOUR

T1 - Carbonyl Propargylation from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Enynes as Surrogates to Preformed Allenylmetal Reagents

T2 - A Ruthenium-Catalyzed C–C Bond-Forming Transfer Hydrogenation

AU - Patman, RL

AU - Williams, VM

AU - Bower, JF

AU - Krische, MJ

PY - 2008

Y1 - 2008

N2 - Transcending oxidation level: Under the conditions of ruthenium-catalyzed transfer hydrogenation, conjugated enynes couple to benzylic, allylic, and aliphatic alcohols or aldehydes to furnish products of carbonyl propargylation (see scheme; dppf=1,1′-bis(diphenylphosphino)ferrocene, TBS=tert-butyldimethylsilyl). Isotopic labeling studies corroborate a mechanism involving hydrogen donation from the alcohol to the enyne.

AB - Transcending oxidation level: Under the conditions of ruthenium-catalyzed transfer hydrogenation, conjugated enynes couple to benzylic, allylic, and aliphatic alcohols or aldehydes to furnish products of carbonyl propargylation (see scheme; dppf=1,1′-bis(diphenylphosphino)ferrocene, TBS=tert-butyldimethylsilyl). Isotopic labeling studies corroborate a mechanism involving hydrogen donation from the alcohol to the enyne.

U2 - 10.1002/anie.200801359

DO - 10.1002/anie.200801359

M3 - Article (Academic Journal)

C2 - 18528831

VL - 47

SP - 5220

EP - 5223

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 28

ER -

Carbonyl Propargylation from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Enynes as Surrogates to Preformed Allenylmetal Reagents: A Ruthenium-Catalyzed C–C Bond-Forming Transfer Hydrogenation

Abstract

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