Angewandte Chemie - International Edition, volume 47, issue 28, pages 5220-5223

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

Ryan L Patman ¹

Vanessa M Williams ²

John Eric Bower ²

Michael J Krische ²

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University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station – A5300, Austin, TX 78712‐1167 (USA) |

University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station – A5300, Austin, TX 78712‐1167, USA, Fax: (+1) 512‐471‐8696 |

Publication type: Journal Article

Publication date: 2008-06-27

Wiley

Journal: Angewandte Chemie - International Edition

Quartile SCImago

Quartile WOS

Impact factor: 16.6

ISSN: 14337851, 15213773

DOI: 10.1002/anie.200801359

Copy DOI

PubMed ID: 18528831

General Chemistry

Catalysis

Abstract

Over the past half century, numerous protocols for carbonyl propargylation using allenylmetal reagents have been developed.[1] Allenic Grignard reagents were used by Prevost et al.[2a] in carbonyl additions to furnish mixtures of β-acetylenic and α-allenic carbinols, which led to them to coin the term “propargylic transposition.”[2a,b] Subsequent studies by Chodkiewicz and co-workers[2c] demonstrated relative stereocontrol in such additions. Shortly thereafter, Lequam and Guillerm[2d] reported that isolable allenic stannanes provide products of carbonyl propargylation upon exposure to chloral. Later, Mukaiyama and Harada[2e] demonstrated that stannanes generated in situ from propargyl iodides and stannous chloride reacted with aldehydes to provide mixtures of β-acetylenic and α-allenic carbinols. Related propargylations employing allenylboron reagents were first reported by Favre and Gaudemar,[2f] and propargylations employing allenylsilicon reagents were first reported by Danheiser and Carini.[2g] Asymmetric variants followed (Scheme 1). Allenylboron reagents chirally modified at the boron center engage in asymmetric propargylation, as was first reported by Yamamoto and co-workers[2h] and Corey et al.[2i] Allenylstannanes chirally modified at the tin center also induce asymmetric carbonyl propargylation, as was first reported by Minowa and Mukaiyama.[2j] Axially chiral allenylstannanes, allenylsilanes, and allenylboron reagents propargylate aldehydes enantiospecifically, as was first described by Marshall et al.,[2k,l] and Hayashi and coworkers,[2m] respectively. Finally, asymmetric aldehyde propargylation using allenylmetal reagents may be catalyzed by chiral Lewis acids or chiral Lewis bases, as was first reported by Keck et al.,[2n] and Denmark and Wynn,[2o] respectively. Scheme 1 Chirally modified allenylmetal reagents for carbonyl propargylation. Tf =trifluoromethanesulfonyl, Ts =para-toluenesulfonyl. Here, we report a new approach to carbonyl propargylation based on ruthenium-catalyzed C–C bond-forming transfer hydrogenation.[3–5] Specifically, upon exposure of 1,3-enynes 1a–1g to alcohols 2a–2o in the presence of [RuHCl(CO)(PPh3)3]/dppf (dppf =1,1′-bis(diphenylphosphino)ferrocene), hydrogen shuffling between reactants occurs to generate nucleophile–electrophile pairs that regioselectively combine to furnish products of carbonyl propargylation.[6] Under related transfer hydrogenation conditions and employing isopropanol as the terminal reductant, 1,3-enynes couple to aldehydes to furnish identical products of carbonyl propargylation. The observed regiochemistry is unique with respect to related enyne–carbonyl reductive coupling reactions that are catalyzed by rhodium[5,7] and nickel complexes, [8,9,10] which favor coupling at the acetylenic terminus of the enyne. Significantly, this protocol enables carbonyl propargylation from the alcohol or aldehyde oxidation level in the absence of preformed allenylmetal reagents (Scheme 2). Scheme 2 Divergent regioselectivity observed in metal-catalyzed enyne–carbonyl coupling. In connection with our efforts to exploit catalytic hydrogenation in C–C coupling reactions beyond hydroformylation,[5] we recently demonstrated that C–C bond formation may be achieved under the conditions of iridium- and ruthenium-catalyzed transfer hydrogenation.[11] These processes enable direct carbonyl allylation from the alcohol or aldehyde oxidation level by using commercially available allenes or dienes as allyl donors. Seeking to develop corresponding carbonyl propargylations, diverse iridium and ruthenium complexes were assayed for their ability to catalyze the coupling of enyne 1a and alcohol 2a. Gratifyingly, both [{Ir(cod)Cl}2]/biphep (biphep =diphenylphosphine, cod =cycloocta-l,5-diene) and [RuHCl(CO)(PPh3)3]/dppf catalyze the desired coupling. The ruthenium-based catalyst was most effective and, under optimized conditions, enyne 1a coupled to benzylic, allylic, and aliphatic alcohols 2a–2o to form homopropargyl alcohols 3a–3o in good to excellent yields (Table 1). To probe the scope of the enyne coupling partner, enynes 1b–1g were coupled to benzyl alcohol 2b under standard reaction conditions. Good to excellent yields of propargylation products 3p–3u were observed (Table 2). Substitution at the olefinic terminus of the enyne was found to diminish conversion to product. Finally, carbonyl allylation can also be achieved from the aldehyde oxidation level by employing isopropanol as the terminal reductant. Under standard reaction conditions, aldehydes 4a–4c couple to enyne 1a to provide the products of carbonyl propargylation 3a–3c, respectively, in good to excellent yield. Thus, carbonyl propargylation may be achieved from either the alcohol or aldehyde oxidation level (Table 3). The coupling products 3a–3u are remarkably resistant to over-oxidation to form the corresponding β,γ-acetylenic ketones. However, such over-oxidation is observed if cationic ruthenium complexes are employed as catalysts. This result suggests that, for the neutral ruthenium complexes employed in this study, the alkyne moiety of the coupling product blocks a coordination site required for β hydride elimination of the carbinol C–H bond. Other aspects of the catalytic mechanism, including determination of the structural and interactive features of the ruthenium complex that influence relative and absolute stereocontrol, are currently under investigation. Table 1 Carbonyl propargylation from the alcohol oxidation level by ruthenium-catalyzed transfer hydrogenation.a Table 2 Coupling of enynes 1b–1g to benzyl alcohol 2b by ruthenium-catalyzed transfer hydrogenation.a Table 3 Carbonyl propargylation from the aldehyde oxidation level by ruthenium-catalyzed transfer hydrogenation.a A general catalytic mechanism is likely to involve the following steps:[11] a) alcohol dehydrogenation to generate a ruthenium hydride is followed by b) enyne hydrometalation to generate an allenyl metal–aldehyde/nucleophile–electrophile pair, which undergoes c) carbonyl addition with propargylic transposition. Consistent with this interpretation, the coupling of enyne 1a to [D]-2b under standard reaction conditions provides [D]-3b, in which deuterium is incorporated at the benzylic position (>95%), the allylic methyl group (56%), and the allylic methine position (24%), thus suggesting reversible olefin-hydrometalation [Eq. (1)]. (1) Our collective studies on hydrogenative and transfer hydrogenative C–C coupling define a departure from the use of preformed organometallic reagents in carbonyl addition chemistry.[5,11] For such transfer hydrogenative coupling reactions, hydrogen embedded within isopropanol or an alcohol substrate is redistributed among reactants to generate nucleophile–electrophile pairs, thus enabling carbonyl addition from the aldehyde or alcohol oxidation level. In this way, carbonyl additions that transcend the boundaries of oxidation level are devised. In the present study, we have demonstrated that 1,3-enynes serve as allenylmetal equivalents under the conditions of transfer hydrogenative coupling, thus also enabling carbonyl propargylation from the alcohol or aldehyde oxidation level. These studies contribute to a growing body of catalytic methods for the direct functionalization of carbinol C–H bonds.[11,12] Future studies will focus on the development of related alcohol–unsaturate C–C coupling processes.

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Journal of the American Chemical Society	Journal of the American Chemical Society, 10, 9.43% Journal of the American Chemical Society 10 publications, 9.43%
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Chemical Reviews	Chemical Reviews, 3, 2.83% Chemical Reviews 3 publications, 2.83%
Chemical Society Reviews	Chemical Society Reviews, 2, 1.89% Chemical Society Reviews 2 publications, 1.89%
Tetrahedron Letters	Tetrahedron Letters, 2, 1.89% Tetrahedron Letters 2 publications, 1.89%
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ACS Catalysis	ACS Catalysis, 2, 1.89% ACS Catalysis 2 publications, 1.89%
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Synlett	Synlett, 2, 1.89% Synlett 2 publications, 1.89%
Chemistry Letters	Chemistry Letters, 1, 0.94% Chemistry Letters 1 publication, 0.94%
Chinese Journal of Organic Chemistry	Chinese Journal of Organic Chemistry, 1, 0.94% Chinese Journal of Organic Chemistry 1 publication, 0.94%
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry	Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 1, 0.94% Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry 1 publication, 0.94%
Science China Chemistry	Science China Chemistry, 1, 0.94% Science China Chemistry 1 publication, 0.94%
Topics in Current Chemistry	Topics in Current Chemistry, 1, 0.94% Topics in Current Chemistry 1 publication, 0.94%
Chinese Chemical Letters	Chinese Chemical Letters, 1, 0.94% Chinese Chemical Letters 1 publication, 0.94%
Inorganic Chemistry Communication	Inorganic Chemistry Communication, 1, 0.94% Inorganic Chemistry Communication 1 publication, 0.94%
Coordination Chemistry Reviews	Coordination Chemistry Reviews, 1, 0.94% Coordination Chemistry Reviews 1 publication, 0.94%
ChemCatChem	ChemCatChem, 1, 0.94% ChemCatChem 1 publication, 0.94%
ChemistrySelect	ChemistrySelect, 1, 0.94% ChemistrySelect 1 publication, 0.94%
ChemInform	ChemInform, 1, 0.94% ChemInform 1 publication, 0.94%
Accounts of Chemical Research	Accounts of Chemical Research, 1, 0.94% Accounts of Chemical Research 1 publication, 0.94%
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Wiley	Wiley, 37, 34.91% Wiley 37 publications, 34.91%
American Chemical Society (ACS)	American Chemical Society (ACS), 31, 29.25% American Chemical Society (ACS) 31 publications, 29.25%
Elsevier	Elsevier, 13, 12.26% Elsevier 13 publications, 12.26%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 11, 10.38% Royal Society of Chemistry (RSC) 11 publications, 10.38%
Springer Nature	Springer Nature, 4, 3.77% Springer Nature 4 publications, 3.77%
American Association for the Advancement of Science (AAAS)	American Association for the Advancement of Science (AAAS), 2, 1.89% American Association for the Advancement of Science (AAAS) 2 publications, 1.89%
Thieme	Thieme, 2, 1.89% Thieme 2 publications, 1.89%
The Chemical Society of Japan	The Chemical Society of Japan, 1, 0.94% The Chemical Society of Japan 1 publication, 0.94%
Shanghai Institute of Organic Chemistry	Shanghai Institute of Organic Chemistry, 1, 0.94% Shanghai Institute of Organic Chemistry 1 publication, 0.94%
Society of Synthetic Organic Chemistry	Society of Synthetic Organic Chemistry, 1, 0.94% Society of Synthetic Organic Chemistry 1 publication, 0.94%
Walter de Gruyter	Walter de Gruyter, 1, 0.94% Walter de Gruyter 1 publication, 0.94%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 0.94% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 0.94%
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Patman R. L. et al. 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. 2008. Vol. 47. No. 28. pp. 5220-5223.

GOST all authors (up to 50) Copy

Patman R. L., Williams V. M., Bower J. E., Krische M. J. 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. 2008. Vol. 47. No. 28. pp. 5220-5223.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1002/anie.200801359

UR - https://doi.org/10.1002/anie.200801359

TI - 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

T2 - Angewandte Chemie - International Edition

AU - Patman, Ryan L

AU - Williams, Vanessa M

AU - Bower, John Eric

AU - Krische, Michael J

PY - 2008

DA - 2008/06/27 00:00:00

PB - Wiley

SP - 5220-5223

IS - 28

VL - 47

PMID - 18528831

SN - 1433-7851

SN - 1521-3773

ER -

BibTex |

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BibTex Copy

@article{2008_Patman,

author = {Ryan L Patman and Vanessa M Williams and John Eric Bower and Michael J Krische},

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},

journal = {Angewandte Chemie - International Edition},

year = {2008},

volume = {47},

publisher = {Wiley},

month = {jun},

url = {https://doi.org/10.1002/anie.200801359},

number = {28},

pages = {5220--5223},

doi = {10.1002/anie.200801359}

}

MLA

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MLA Copy

Patman, Ryan L., et al. “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, Jun. 2008, pp. 5220-5223. https://doi.org/10.1002/anie.200801359.

Found error?

Publisher

Wiley

Journal

Angewandte Chemie - International Edition

Quartile SCImago

Quartile WOS

Impact factor

16.6

ISSN

14337851 (Print)
15213773 (Electronic)