Cu(I)-Catalyzed 1,2-Alkynyl-propargylation and -benzylation of Benzyne Derivatives

Qile Wang; Thomas R. Hoye

doi:10.1021/acs.orglett.1c01788

Cu(I)-Catalyzed 1,2-Alkynyl-propargylation and -benzylation of Benzyne Derivatives

Qile Wang, Thomas R. Hoye

Chemistry (Twin Cities)

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

Abstract

We report here a three-component, Cu(I)-catalyzed hexadehydro-Diels-Alder (HDDA) benzyne 1,2-difunctionalization reaction. This protocol allowed the introduction of two different carbon-based substituents onto the in situ-generated benzyne. These substituents were terminal monoynes or diynes partnered with propargylic, benzylic, or allylic chlorides. An example of a sequential HDDA reaction is demonstrated using the product of a 1,3-diyne and a propargylic halide, itself a newly created HDDA precursor.

Original language	English (US)
Pages (from-to)	5448-5451
Number of pages	4
Journal	Organic Letters
Volume	23
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.1c01788
State	Published - Jul 16 2021

Bibliographical note

Funding Information:
This research was supported by the National Science Foundation (CHE-1665389) and the National Institute of General Medical Sciences of the National Institutes of Health (NIH) (R35 GM127097). Some of the NMR spectral data were acquired with instrumentation acquired with funding through an NIH Shared Instrumentation Grant (S10OD011952). Mass spectrometry was performed in the Analytical Biochemistry Shared Resource laboratory of the University of Minnesota, Masonic Cancer Center, which was partially funded by a Cancer Center Support Grant (CA-77598).

Publisher Copyright:
© 2021 American Chemical Society.

PubMed: MeSH publication types

Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

Access

10.1021/acs.orglett.1c01788

Cite this

@article{5b0e7b8947624a91966a0b3f65fe75d6,

title = "Cu(I)-Catalyzed 1,2-Alkynyl-propargylation and -benzylation of Benzyne Derivatives",

abstract = "We report here a three-component, Cu(I)-catalyzed hexadehydro-Diels-Alder (HDDA) benzyne 1,2-difunctionalization reaction. This protocol allowed the introduction of two different carbon-based substituents onto the in situ-generated benzyne. These substituents were terminal monoynes or diynes partnered with propargylic, benzylic, or allylic chlorides. An example of a sequential HDDA reaction is demonstrated using the product of a 1,3-diyne and a propargylic halide, itself a newly created HDDA precursor.",

author = "Qile Wang and Hoye, {Thomas R.}",

note = "Funding Information: This research was supported by the National Science Foundation (CHE-1665389) and the National Institute of General Medical Sciences of the National Institutes of Health (NIH) (R35 GM127097). Some of the NMR spectral data were acquired with instrumentation acquired with funding through an NIH Shared Instrumentation Grant (S10OD011952). Mass spectrometry was performed in the Analytical Biochemistry Shared Resource laboratory of the University of Minnesota, Masonic Cancer Center, which was partially funded by a Cancer Center Support Grant (CA-77598). Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = jul,

day = "16",

doi = "10.1021/acs.orglett.1c01788",

language = "English (US)",

volume = "23",

pages = "5448--5451",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - Cu(I)-Catalyzed 1,2-Alkynyl-propargylation and -benzylation of Benzyne Derivatives

AU - Wang, Qile

AU - Hoye, Thomas R.

N1 - Funding Information: This research was supported by the National Science Foundation (CHE-1665389) and the National Institute of General Medical Sciences of the National Institutes of Health (NIH) (R35 GM127097). Some of the NMR spectral data were acquired with instrumentation acquired with funding through an NIH Shared Instrumentation Grant (S10OD011952). Mass spectrometry was performed in the Analytical Biochemistry Shared Resource laboratory of the University of Minnesota, Masonic Cancer Center, which was partially funded by a Cancer Center Support Grant (CA-77598). Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/7/16

Y1 - 2021/7/16

N2 - We report here a three-component, Cu(I)-catalyzed hexadehydro-Diels-Alder (HDDA) benzyne 1,2-difunctionalization reaction. This protocol allowed the introduction of two different carbon-based substituents onto the in situ-generated benzyne. These substituents were terminal monoynes or diynes partnered with propargylic, benzylic, or allylic chlorides. An example of a sequential HDDA reaction is demonstrated using the product of a 1,3-diyne and a propargylic halide, itself a newly created HDDA precursor.

AB - We report here a three-component, Cu(I)-catalyzed hexadehydro-Diels-Alder (HDDA) benzyne 1,2-difunctionalization reaction. This protocol allowed the introduction of two different carbon-based substituents onto the in situ-generated benzyne. These substituents were terminal monoynes or diynes partnered with propargylic, benzylic, or allylic chlorides. An example of a sequential HDDA reaction is demonstrated using the product of a 1,3-diyne and a propargylic halide, itself a newly created HDDA precursor.

UR - http://www.scopus.com/inward/record.url?scp=85110253482&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85110253482&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.1c01788

DO - 10.1021/acs.orglett.1c01788

M3 - Article

C2 - 34180676

AN - SCOPUS:85110253482

VL - 23

SP - 5448

EP - 5451

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 14

ER -

Cu(I)-Catalyzed 1,2-Alkynyl-propargylation and -benzylation of Benzyne Derivatives

Abstract

Bibliographical note

PubMed: MeSH publication types

Access

Other files and links

Fingerprint

Cite this