Ni-Catalyzed Regioselective β,δ-Diarylation of Unactivated Olefins in Ketimines via Ligand-Enabled Contraction of Transient Nickellacycles: Rapid Access to Remotely Diarylated Ketones

Prakash Basnet; Roshan K. Dhungana; Surendra Thapa; Bijay Shrestha; Shekhar Kc; Jeremiah M. Sears; Ramesh Giri

doi:10.1021/jacs.8b03163

Ni-Catalyzed Regioselective β,δ-Diarylation of Unactivated Olefins in Ketimines via Ligand-Enabled Contraction of Transient Nickellacycles: Rapid Access to Remotely Diarylated Ketones

Prakash Basnet, Roshan K. Dhungana, Surendra Thapa, Bijay Shrestha, Shekhar Kc, Jeremiah M. Sears, Ramesh Giri

Chemistry

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126 Scopus citations

Abstract

We disclose a [(PhO) ₃ P]/NiBr ₂ -catalyzed regioselective β, δ-diarylation of unactivated olefins in ketimines with aryl halides and arylzinc reagents. This diarylation proceeds at remote locations to the carbonyl group to afford, after simple H ⁺ workup, diversely substituted β, δ-diarylketones that are otherwise difficult to access readily with existing methods. Deuterium-labeling and crossover experiments indicate that diarylation proceeds by ligand-enabled contraction of transient nickellacycles.

Original language	English (US)
Pages (from-to)	7782-7786
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	140
Issue number	25
DOIs	https://doi.org/10.1021/jacs.8b03163
State	Published - Jun 27 2018

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.8b03163

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Basnet, P., Dhungana, R. K., Thapa, S., Shrestha, B., Kc, S., Sears, J. M., & Giri, R. (2018). Ni-Catalyzed Regioselective β,δ-Diarylation of Unactivated Olefins in Ketimines via Ligand-Enabled Contraction of Transient Nickellacycles: Rapid Access to Remotely Diarylated Ketones. Journal of the American Chemical Society, 140(25), 7782-7786. https://doi.org/10.1021/jacs.8b03163

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title = "Ni-Catalyzed Regioselective β,δ-Diarylation of Unactivated Olefins in Ketimines via Ligand-Enabled Contraction of Transient Nickellacycles: Rapid Access to Remotely Diarylated Ketones",

abstract = " We disclose a [(PhO) 3 P]/NiBr 2 -catalyzed regioselective β, δ-diarylation of unactivated olefins in ketimines with aryl halides and arylzinc reagents. This diarylation proceeds at remote locations to the carbonyl group to afford, after simple H + workup, diversely substituted β, δ-diarylketones that are otherwise difficult to access readily with existing methods. Deuterium-labeling and crossover experiments indicate that diarylation proceeds by ligand-enabled contraction of transient nickellacycles. ",

author = "Prakash Basnet and Dhungana, {Roshan K.} and Surendra Thapa and Bijay Shrestha and Shekhar Kc and Sears, {Jeremiah M.} and Ramesh Giri",

note = "Funding Information: We thank the University of New Mexico (UNM) and the National Science Foundation (NSF CHE-1554299) for financial support and upgrades to the NMR (NSF grants CHE08-40523 and CHE09-46690) and MS Facilities. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = jun,

day = "27",

doi = "10.1021/jacs.8b03163",

language = "English (US)",

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Basnet, P, Dhungana, RK, Thapa, S, Shrestha, B, Kc, S, Sears, JM & Giri, R 2018, 'Ni-Catalyzed Regioselective β,δ-Diarylation of Unactivated Olefins in Ketimines via Ligand-Enabled Contraction of Transient Nickellacycles: Rapid Access to Remotely Diarylated Ketones', Journal of the American Chemical Society, vol. 140, no. 25, pp. 7782-7786. https://doi.org/10.1021/jacs.8b03163

Ni-Catalyzed Regioselective β,δ-Diarylation of Unactivated Olefins in Ketimines via Ligand-Enabled Contraction of Transient Nickellacycles: Rapid Access to Remotely Diarylated Ketones. / Basnet, Prakash; Dhungana, Roshan K.; Thapa, Surendra et al.
In: Journal of the American Chemical Society, Vol. 140, No. 25, 27.06.2018, p. 7782-7786.

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

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T1 - Ni-Catalyzed Regioselective β,δ-Diarylation of Unactivated Olefins in Ketimines via Ligand-Enabled Contraction of Transient Nickellacycles

T2 - Rapid Access to Remotely Diarylated Ketones

AU - Basnet, Prakash

AU - Dhungana, Roshan K.

AU - Thapa, Surendra

AU - Shrestha, Bijay

AU - Kc, Shekhar

AU - Sears, Jeremiah M.

AU - Giri, Ramesh

N1 - Funding Information: We thank the University of New Mexico (UNM) and the National Science Foundation (NSF CHE-1554299) for financial support and upgrades to the NMR (NSF grants CHE08-40523 and CHE09-46690) and MS Facilities. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/6/27

Y1 - 2018/6/27

N2 - We disclose a [(PhO) 3 P]/NiBr 2 -catalyzed regioselective β, δ-diarylation of unactivated olefins in ketimines with aryl halides and arylzinc reagents. This diarylation proceeds at remote locations to the carbonyl group to afford, after simple H + workup, diversely substituted β, δ-diarylketones that are otherwise difficult to access readily with existing methods. Deuterium-labeling and crossover experiments indicate that diarylation proceeds by ligand-enabled contraction of transient nickellacycles.

AB - We disclose a [(PhO) 3 P]/NiBr 2 -catalyzed regioselective β, δ-diarylation of unactivated olefins in ketimines with aryl halides and arylzinc reagents. This diarylation proceeds at remote locations to the carbonyl group to afford, after simple H + workup, diversely substituted β, δ-diarylketones that are otherwise difficult to access readily with existing methods. Deuterium-labeling and crossover experiments indicate that diarylation proceeds by ligand-enabled contraction of transient nickellacycles.

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Ni-Catalyzed Regioselective β,δ-Diarylation of Unactivated Olefins in Ketimines via Ligand-Enabled Contraction of Transient Nickellacycles: Rapid Access to Remotely Diarylated Ketones

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