Tandem Ullmann-Goldberg Cross-Coupling/Cyclopalladation-Reductive Elimination Reactions and Related Sequences Leading to Polyfunctionalized Benzofurans, Indoles, and Phthalanes

Faiyaz Khan; Mehvish Fatima; Moheb Shirzaei; Yen Vo; Madushani Amarasiri; Martin G. Banwell; Chenxi Ma; Jas S. Ward; Michael G. Gardiner

doi:10.1021/acs.orglett.9b02235

Tandem Ullmann-Goldberg Cross-Coupling/Cyclopalladation-Reductive Elimination Reactions and Related Sequences Leading to Polyfunctionalized Benzofurans, Indoles, and Phthalanes

Faiyaz Khan, Mehvish Fatima, Moheb Shirzaei, Yen Vo, Madushani Amarasiri, Martin G. Banwell^*, Chenxi Ma, Jas S. Ward, Michael G. Gardiner

^*Corresponding author for this work

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

22 Citations (Scopus)

Abstract

On exposure to a combination of Cu[I]- and Pd[0]-based catalysts, compounds such as 1 and 7 engage in tandem Ullmann-Goldberg cross-coupling and cyclopalladation-reductive elimination reactions to give benzofurans such as 8. Related reactions involving hetero-Michael additions of o-halogenated phenols or anilines to propiolates and the Pd[0]-catalyzed cyclization of the resulting conjugates provide, in a one-pot process, alternately functionalized benzofurans, indoles, or phthalanes.

Original language	English
Pages (from-to)	6342-6346
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.9b02235
Publication status	Published - 16 Aug 2019

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Khan, F., Fatima, M., Shirzaei, M., Vo, Y., Amarasiri, M., Banwell, M. G., Ma, C., Ward, J. S., & Gardiner, M. G. (2019). Tandem Ullmann-Goldberg Cross-Coupling/Cyclopalladation-Reductive Elimination Reactions and Related Sequences Leading to Polyfunctionalized Benzofurans, Indoles, and Phthalanes. Organic Letters, 21(16), 6342-6346. https://doi.org/10.1021/acs.orglett.9b02235

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title = "Tandem Ullmann-Goldberg Cross-Coupling/Cyclopalladation-Reductive Elimination Reactions and Related Sequences Leading to Polyfunctionalized Benzofurans, Indoles, and Phthalanes",

abstract = "On exposure to a combination of Cu[I]- and Pd[0]-based catalysts, compounds such as 1 and 7 engage in tandem Ullmann-Goldberg cross-coupling and cyclopalladation-reductive elimination reactions to give benzofurans such as 8. Related reactions involving hetero-Michael additions of o-halogenated phenols or anilines to propiolates and the Pd[0]-catalyzed cyclization of the resulting conjugates provide, in a one-pot process, alternately functionalized benzofurans, indoles, or phthalanes.",

author = "Faiyaz Khan and Mehvish Fatima and Moheb Shirzaei and Yen Vo and Madushani Amarasiri and Banwell, {Martin G.} and Chenxi Ma and Ward, {Jas S.} and Gardiner, {Michael G.}",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = aug,

day = "16",

doi = "10.1021/acs.orglett.9b02235",

language = "English",

volume = "21",

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journal = "Organic Letters",

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Khan, F, Fatima, M, Shirzaei, M, Vo, Y, Amarasiri, M, Banwell, MG, Ma, C, Ward, JS & Gardiner, MG 2019, 'Tandem Ullmann-Goldberg Cross-Coupling/Cyclopalladation-Reductive Elimination Reactions and Related Sequences Leading to Polyfunctionalized Benzofurans, Indoles, and Phthalanes', Organic Letters, vol. 21, no. 16, pp. 6342-6346. https://doi.org/10.1021/acs.orglett.9b02235

TY - JOUR

T1 - Tandem Ullmann-Goldberg Cross-Coupling/Cyclopalladation-Reductive Elimination Reactions and Related Sequences Leading to Polyfunctionalized Benzofurans, Indoles, and Phthalanes

AU - Khan, Faiyaz

AU - Fatima, Mehvish

AU - Shirzaei, Moheb

AU - Vo, Yen

AU - Amarasiri, Madushani

AU - Banwell, Martin G.

AU - Ma, Chenxi

AU - Ward, Jas S.

AU - Gardiner, Michael G.

PY - 2019/8/16

Y1 - 2019/8/16

N2 - On exposure to a combination of Cu[I]- and Pd[0]-based catalysts, compounds such as 1 and 7 engage in tandem Ullmann-Goldberg cross-coupling and cyclopalladation-reductive elimination reactions to give benzofurans such as 8. Related reactions involving hetero-Michael additions of o-halogenated phenols or anilines to propiolates and the Pd[0]-catalyzed cyclization of the resulting conjugates provide, in a one-pot process, alternately functionalized benzofurans, indoles, or phthalanes.

AB - On exposure to a combination of Cu[I]- and Pd[0]-based catalysts, compounds such as 1 and 7 engage in tandem Ullmann-Goldberg cross-coupling and cyclopalladation-reductive elimination reactions to give benzofurans such as 8. Related reactions involving hetero-Michael additions of o-halogenated phenols or anilines to propiolates and the Pd[0]-catalyzed cyclization of the resulting conjugates provide, in a one-pot process, alternately functionalized benzofurans, indoles, or phthalanes.

UR - http://www.scopus.com/inward/record.url?scp=85070674007&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.9b02235

DO - 10.1021/acs.orglett.9b02235

M3 - Article

SN - 1523-7060

VL - 21

SP - 6342

EP - 6346

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

Tandem Ullmann-Goldberg Cross-Coupling/Cyclopalladation-Reductive Elimination Reactions and Related Sequences Leading to Polyfunctionalized Benzofurans, Indoles, and Phthalanes

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