Verkade Base in FLP Chemistry-From Stoichiometric C-H Bond Cleavage to the Catalytic Dimerization of Alkynes

Amandeep Brar; Suresh Mummadi; Daniel K. Unruh; Clemens Krempner

doi:10.1021/acs.organomet.0c00411

Verkade Base in FLP Chemistry-From Stoichiometric C-H Bond Cleavage to the Catalytic Dimerization of Alkynes

Amandeep Brar, Suresh Mummadi, Daniel K. Unruh, Clemens Krempner

Chemistry and Biochemistry

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

Abstract

Stoichiometric and catalytic reactions of terminal alkynes with various FLPs and Lewis acid-base adducts have been investigated. Reactions of phenylacetylene with FLPs composed of the Verkade base N[CH₂CH₂NPrⁱ]₃P (1) and the Lewis acids BPh₃, 9-hexyl-BBN, and 9-BBN gave [N(CH₂CH₂NPrⁱ)₃PH][PhCC-BPh₃] (2), [N(CH₂CH₂NPrⁱ)₃PH][9-hexyl-9-PhCC-BBN] (3), and [N(CH₂CH₂NPrⁱ)₃PH][9-PhCH=CH-9-PhCC-BBN] (4). The binuclear Lewis acid-base adduct (C₆F₅)₃Al-N[CH₂CH₂NPrⁱ]₃P-Al(C₆F₅)₃(6) effectively catalyzed the dimerization of terminal alkynes to gem-1,3-enynes.

Original language	English
Pages (from-to)	4307-4311
Number of pages	5
Journal	Organometallics
Volume	39
Issue number	23
DOIs	https://doi.org/10.1021/acs.organomet.0c00411
State	Published - Dec 14 2020

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@article{818920b2991a4700b1cf4e638ab6113f,

title = "Verkade Base in FLP Chemistry-From Stoichiometric C-H Bond Cleavage to the Catalytic Dimerization of Alkynes",

abstract = "Stoichiometric and catalytic reactions of terminal alkynes with various FLPs and Lewis acid-base adducts have been investigated. Reactions of phenylacetylene with FLPs composed of the Verkade base N[CH2CH2NPri]3P (1) and the Lewis acids BPh3, 9-hexyl-BBN, and 9-BBN gave [N(CH2CH2NPri)3PH][PhCC-BPh3] (2), [N(CH2CH2NPri)3PH][9-hexyl-9-PhCC-BBN] (3), and [N(CH2CH2NPri)3PH][9-PhCH=CH-9-PhCC-BBN] (4). The binuclear Lewis acid-base adduct (C6F5)3Al-N[CH2CH2NPri]3P-Al(C6F5)3(6) effectively catalyzed the dimerization of terminal alkynes to gem-1,3-enynes.",

author = "Amandeep Brar and Suresh Mummadi and Unruh, {Daniel K.} and Clemens Krempner",

year = "2020",

month = dec,

day = "14",

doi = "10.1021/acs.organomet.0c00411",

language = "English",

volume = "39",

pages = "4307--4311",

journal = "Organometallics",

issn = "0276-7333",

number = "23",

}

TY - JOUR

T1 - Verkade Base in FLP Chemistry-From Stoichiometric C-H Bond Cleavage to the Catalytic Dimerization of Alkynes

AU - Brar, Amandeep

AU - Mummadi, Suresh

AU - Unruh, Daniel K.

AU - Krempner, Clemens

PY - 2020/12/14

Y1 - 2020/12/14

N2 - Stoichiometric and catalytic reactions of terminal alkynes with various FLPs and Lewis acid-base adducts have been investigated. Reactions of phenylacetylene with FLPs composed of the Verkade base N[CH2CH2NPri]3P (1) and the Lewis acids BPh3, 9-hexyl-BBN, and 9-BBN gave [N(CH2CH2NPri)3PH][PhCC-BPh3] (2), [N(CH2CH2NPri)3PH][9-hexyl-9-PhCC-BBN] (3), and [N(CH2CH2NPri)3PH][9-PhCH=CH-9-PhCC-BBN] (4). The binuclear Lewis acid-base adduct (C6F5)3Al-N[CH2CH2NPri]3P-Al(C6F5)3(6) effectively catalyzed the dimerization of terminal alkynes to gem-1,3-enynes.

AB - Stoichiometric and catalytic reactions of terminal alkynes with various FLPs and Lewis acid-base adducts have been investigated. Reactions of phenylacetylene with FLPs composed of the Verkade base N[CH2CH2NPri]3P (1) and the Lewis acids BPh3, 9-hexyl-BBN, and 9-BBN gave [N(CH2CH2NPri)3PH][PhCC-BPh3] (2), [N(CH2CH2NPri)3PH][9-hexyl-9-PhCC-BBN] (3), and [N(CH2CH2NPri)3PH][9-PhCH=CH-9-PhCC-BBN] (4). The binuclear Lewis acid-base adduct (C6F5)3Al-N[CH2CH2NPri]3P-Al(C6F5)3(6) effectively catalyzed the dimerization of terminal alkynes to gem-1,3-enynes.

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U2 - 10.1021/acs.organomet.0c00411

DO - 10.1021/acs.organomet.0c00411

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JO - Organometallics

JF - Organometallics

SN - 0276-7333

IS - 23

ER -