Nickel Phosphite-Catalyzed Tetradehydro-Diels-Alder Reactions of (E)-3-ene-1,8-diynes

Liam M. Joyce; Stephen A. Moggach; Christopher J.T. Hyland; Stephen G. Pyne; Scott G. Stewart

doi:10.1021/acs.joc.2c03040

Nickel Phosphite-Catalyzed Tetradehydro-Diels-Alder Reactions of (E)-3-ene-1,8-diynes

Liam M. Joyce
, Stephen A. Moggach
, Christopher J.T. Hyland
, Stephen G. Pyne
, Scott G. Stewart

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

A nickel-catalyzed tetradehydro-Diels-Alder reaction of (E)-3-ene-1,8-diynes for the preparation of isoindolines, dihydroisobenzofurans, and tetrahydroisoquinolines has been developed. A series of air-stable nickel catalysts were used in this study, including the novel nickel(0)-phosphite catalysts, Ni[P(O-3,5-Me-Ph)₃]₄, Ni[P(O-1-naphthyl)₃]₄, and Ni[P(O-2-naphthyl)₃]₄. To help understand the type of intermediate in the initial cycloisomerization process, the trapping of nickellacycle intermediates with pinacolborane to yield vinyl boronates is also discussed.

Original language	English
Pages (from-to)	5391-5402
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	88
Issue number	9
DOIs	https://doi.org/10.1021/acs.joc.2c03040
Publication status	Published - 5 May 2023

Funding

Funders	Funder number
ARC Australian Research Council	DP180101332, FT200100243

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10.1021/acs.joc.2c03040

Cite this

@article{70a83280cfa14c38b1702527bf87a015,

title = "Nickel Phosphite-Catalyzed Tetradehydro-Diels-Alder Reactions of (E)-3-ene-1,8-diynes",

abstract = "A nickel-catalyzed tetradehydro-Diels-Alder reaction of (E)-3-ene-1,8-diynes for the preparation of isoindolines, dihydroisobenzofurans, and tetrahydroisoquinolines has been developed. A series of air-stable nickel catalysts were used in this study, including the novel nickel(0)-phosphite catalysts, Ni[P(O-3,5-Me-Ph)3]4, Ni[P(O-1-naphthyl)3]4, and Ni[P(O-2-naphthyl)3]4. To help understand the type of intermediate in the initial cycloisomerization process, the trapping of nickellacycle intermediates with pinacolborane to yield vinyl boronates is also discussed.",

author = "Joyce, \{Liam M.\} and Moggach, \{Stephen A.\} and Hyland, \{Christopher J.T.\} and Pyne, \{Stephen G.\} and Stewart, \{Scott G.\}",

note = "Funding Information: Grants and Scholarship. The authors acknowledge Australian Research Council Discovery grant DP180101332 for partially funding different aspects of this project. Support from the CMCA Research Facility at UWA is recognized. Further NMR assistance from Dr. Gareth Nealon (UWA) is gratefully acknowledged. L.M.J. is a recipient of an APA scholarship through the University of Wollongong. Prof. Moggach is a appreciative recipient of an ARC ARC Future Fellowships FT200100243. Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

month = may,

day = "5",

doi = "10.1021/acs.joc.2c03040",

language = "English",

volume = "88",

pages = "5391--5402",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Nickel Phosphite-Catalyzed Tetradehydro-Diels-Alder Reactions of (E)-3-ene-1,8-diynes

AU - Joyce, Liam M.

AU - Moggach, Stephen A.

AU - Hyland, Christopher J.T.

AU - Pyne, Stephen G.

AU - Stewart, Scott G.

N1 - Funding Information: Grants and Scholarship. The authors acknowledge Australian Research Council Discovery grant DP180101332 for partially funding different aspects of this project. Support from the CMCA Research Facility at UWA is recognized. Further NMR assistance from Dr. Gareth Nealon (UWA) is gratefully acknowledged. L.M.J. is a recipient of an APA scholarship through the University of Wollongong. Prof. Moggach is a appreciative recipient of an ARC ARC Future Fellowships FT200100243. Publisher Copyright: © 2023 American Chemical Society.

PY - 2023/5/5

Y1 - 2023/5/5

N2 - A nickel-catalyzed tetradehydro-Diels-Alder reaction of (E)-3-ene-1,8-diynes for the preparation of isoindolines, dihydroisobenzofurans, and tetrahydroisoquinolines has been developed. A series of air-stable nickel catalysts were used in this study, including the novel nickel(0)-phosphite catalysts, Ni[P(O-3,5-Me-Ph)3]4, Ni[P(O-1-naphthyl)3]4, and Ni[P(O-2-naphthyl)3]4. To help understand the type of intermediate in the initial cycloisomerization process, the trapping of nickellacycle intermediates with pinacolborane to yield vinyl boronates is also discussed.

AB - A nickel-catalyzed tetradehydro-Diels-Alder reaction of (E)-3-ene-1,8-diynes for the preparation of isoindolines, dihydroisobenzofurans, and tetrahydroisoquinolines has been developed. A series of air-stable nickel catalysts were used in this study, including the novel nickel(0)-phosphite catalysts, Ni[P(O-3,5-Me-Ph)3]4, Ni[P(O-1-naphthyl)3]4, and Ni[P(O-2-naphthyl)3]4. To help understand the type of intermediate in the initial cycloisomerization process, the trapping of nickellacycle intermediates with pinacolborane to yield vinyl boronates is also discussed.

UR - https://www.scopus.com/pages/publications/85152684075

U2 - 10.1021/acs.joc.2c03040

DO - 10.1021/acs.joc.2c03040

M3 - Article

C2 - 37036249

AN - SCOPUS:85152684075

SN - 0022-3263

VL - 88

SP - 5391

EP - 5402

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 9

ER -

Nickel Phosphite-Catalyzed Tetradehydro-Diels-Alder Reactions of (E)-3-ene-1,8-diynes

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Nickel Phosphite-Catalyzed Tetradehydro-Diels-Alder Reactions of (E)-3-ene-1,8-diynes

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