Ni-Catalyzed Regio- and Stereoselective Alkylarylation of Unactivated Alkenes in γ,δ-Alkenylketimines

Vivek Aryal; Lucas J. Chesley; Doleshwar Niroula; Rishi R. Sapkota; Roshan K. Dhungana; Ramesh Giri

doi:10.1021/acscatal.2c01697

Ni-Catalyzed Regio- and Stereoselective Alkylarylation of Unactivated Alkenes in γ,δ-Alkenylketimines

Vivek Aryal, Lucas J. Chesley, Doleshwar Niroula, Rishi R. Sapkota, Roshan K. Dhungana, Ramesh Giri

Chemistry

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

7 Scopus citations

Abstract

We disclose a Ni-catalyzed vicinal alkylarylation of unactivated alkenes in γ,δ-alkenylketimines with aryl halides and alkylzinc reagents. The reaction produces γ-C(sp³)-branched δ-arylketones with the construction of two C(sp³)-C(sp³) and C(sp³)-C(sp²) bonds. Electron-deficient alkenes play crucial dual roles as ligands to stabilize reaction intermediates and to increase catalytic rates for the formation of C(sp³)-C(sp³) bonds. This alkene alkylarylation reaction is also effective for secondary alkylzinc reagents and internal alkenes and proceeds with a complete regio- and stereocontrol, affording products with up to three contiguous all-carbon all-cis secondary stereocenters.

Original language	English (US)
Pages (from-to)	7262-7268
Number of pages	7
Journal	ACS Catalysis
Volume	12
Issue number	12
DOIs	https://doi.org/10.1021/acscatal.2c01697
State	Published - Jun 17 2022

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

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10.1021/acscatal.2c01697

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title = "Ni-Catalyzed Regio- and Stereoselective Alkylarylation of Unactivated Alkenes in γ,δ-Alkenylketimines",

abstract = "We disclose a Ni-catalyzed vicinal alkylarylation of unactivated alkenes in γ,δ-alkenylketimines with aryl halides and alkylzinc reagents. The reaction produces γ-C(sp3)-branched δ-arylketones with the construction of two C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds. Electron-deficient alkenes play crucial dual roles as ligands to stabilize reaction intermediates and to increase catalytic rates for the formation of C(sp3)-C(sp3) bonds. This alkene alkylarylation reaction is also effective for secondary alkylzinc reagents and internal alkenes and proceeds with a complete regio- and stereocontrol, affording products with up to three contiguous all-carbon all-cis secondary stereocenters.",

author = "Vivek Aryal and Chesley, {Lucas J.} and Doleshwar Niroula and Sapkota, {Rishi R.} and Dhungana, {Roshan K.} and Ramesh Giri",

year = "2022",

month = jun,

day = "17",

doi = "10.1021/acscatal.2c01697",

language = "English (US)",

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pages = "7262--7268",

journal = "ACS Catalysis",

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publisher = "American Chemical Society",

number = "12",

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TY - JOUR

T1 - Ni-Catalyzed Regio- and Stereoselective Alkylarylation of Unactivated Alkenes in γ,δ-Alkenylketimines

AU - Aryal, Vivek

AU - Chesley, Lucas J.

AU - Niroula, Doleshwar

AU - Sapkota, Rishi R.

AU - Dhungana, Roshan K.

AU - Giri, Ramesh

PY - 2022/6/17

Y1 - 2022/6/17

N2 - We disclose a Ni-catalyzed vicinal alkylarylation of unactivated alkenes in γ,δ-alkenylketimines with aryl halides and alkylzinc reagents. The reaction produces γ-C(sp3)-branched δ-arylketones with the construction of two C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds. Electron-deficient alkenes play crucial dual roles as ligands to stabilize reaction intermediates and to increase catalytic rates for the formation of C(sp3)-C(sp3) bonds. This alkene alkylarylation reaction is also effective for secondary alkylzinc reagents and internal alkenes and proceeds with a complete regio- and stereocontrol, affording products with up to three contiguous all-carbon all-cis secondary stereocenters.

AB - We disclose a Ni-catalyzed vicinal alkylarylation of unactivated alkenes in γ,δ-alkenylketimines with aryl halides and alkylzinc reagents. The reaction produces γ-C(sp3)-branched δ-arylketones with the construction of two C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds. Electron-deficient alkenes play crucial dual roles as ligands to stabilize reaction intermediates and to increase catalytic rates for the formation of C(sp3)-C(sp3) bonds. This alkene alkylarylation reaction is also effective for secondary alkylzinc reagents and internal alkenes and proceeds with a complete regio- and stereocontrol, affording products with up to three contiguous all-carbon all-cis secondary stereocenters.

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U2 - 10.1021/acscatal.2c01697

DO - 10.1021/acscatal.2c01697

M3 - Article

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AN - SCOPUS:85132101774

SN - 2155-5435

VL - 12

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JO - ACS Catalysis

JF - ACS Catalysis

IS - 12

ER -

Ni-Catalyzed Regio- and Stereoselective Alkylarylation of Unactivated Alkenes in γ,δ-Alkenylketimines

Abstract

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