Organolanthanide-catalyzed cyclodimerizations of disubstituted alkynes

H. J. Heeres; A. Heeres; J. H. Teuben

doi:10.1021/om00119a023

Organolanthanide-catalyzed cyclodimerizations of disubstituted alkynes

H. J. Heeres, A. Heeres, J. H. Teuben

Biobased Ingredients and Materials

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

Abstract

The lanthanide alkyls Cp 2 *LnCH(SiMe 3 ) 2 (Ln = La, Ce) are efficient catalysts for the cyclodimerization of 2-alkynes MeC≡CR (R = Me, Et, n-Pr) to 1,2-disubstituted 3-alkylidenecyclobutenes. The first step in the reaction is a propargylic metalation of the α-methyl group, giving Cp* 2 LnCH 2 C≡CR compounds and free CH 2 (SiMe 3 ) 2 . © 1990, American Chemical Society. All rights reserved.

Original language	English
Pages (from-to)	1508-1510
Journal	Organometallics
Volume	9
Issue number	5
DOIs	https://doi.org/10.1021/om00119a023
Publication status	Published - 1 May 1990

Access to Document

10.1021/om00119a023

http://www.mendeley.com/research/organolanthanidecatalyzed-cyclodimerizations-disubstituted-alkynes

1 Article

GMP Compliant Synthesis of Canagliflozin, a Novel PET Tracer for the Sodium−Glucose Cotransporter 2
Heeres, A., van der Hoek, S., Antunes, I. F., Attia, K. A., Jacquet, O., Bulthuis, M., Zijlma, R., Boersma, H. H., van Goor, H., Visser, T. J., Heerspink, H. J. L., Elsinga, P. H. & Stevens, J., 8 Nov 2021, In: Journal of Medicinal Chemistry.
Research output: Contribution to journal › Article › Academic › peer-review

Open Access
File

Cite this

@article{93cbbd92c91c42fa82bc88f8817f9fa5,

title = "Organolanthanide-catalyzed cyclodimerizations of disubstituted alkynes",

abstract = "The lanthanide alkyls Cp 2 *LnCH(SiMe 3 ) 2 (Ln = La, Ce) are efficient catalysts for the cyclodimerization of 2-alkynes MeC≡CR (R = Me, Et, n-Pr) to 1,2-disubstituted 3-alkylidenecyclobutenes. The first step in the reaction is a propargylic metalation of the α-methyl group, giving Cp* 2 LnCH 2 C≡CR compounds and free CH 2 (SiMe 3 ) 2 . {\textcopyright} 1990, American Chemical Society. All rights reserved.",

author = "Heeres, {H. J.} and A. Heeres and Teuben, {J. H.}",

year = "1990",

month = may,

day = "1",

doi = "10.1021/om00119a023",

language = "English",

volume = "9",

pages = "1508--1510",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - Organolanthanide-catalyzed cyclodimerizations of disubstituted alkynes

AU - Heeres, H. J.

AU - Heeres, A.

AU - Teuben, J. H.

PY - 1990/5/1

Y1 - 1990/5/1

N2 - The lanthanide alkyls Cp 2 *LnCH(SiMe 3 ) 2 (Ln = La, Ce) are efficient catalysts for the cyclodimerization of 2-alkynes MeC≡CR (R = Me, Et, n-Pr) to 1,2-disubstituted 3-alkylidenecyclobutenes. The first step in the reaction is a propargylic metalation of the α-methyl group, giving Cp* 2 LnCH 2 C≡CR compounds and free CH 2 (SiMe 3 ) 2 . © 1990, American Chemical Society. All rights reserved.

AB - The lanthanide alkyls Cp 2 *LnCH(SiMe 3 ) 2 (Ln = La, Ce) are efficient catalysts for the cyclodimerization of 2-alkynes MeC≡CR (R = Me, Et, n-Pr) to 1,2-disubstituted 3-alkylidenecyclobutenes. The first step in the reaction is a propargylic metalation of the α-methyl group, giving Cp* 2 LnCH 2 C≡CR compounds and free CH 2 (SiMe 3 ) 2 . © 1990, American Chemical Society. All rights reserved.

U2 - 10.1021/om00119a023

DO - 10.1021/om00119a023

M3 - Article

SN - 0276-7333

VL - 9

SP - 1508

EP - 1510

JO - Organometallics

JF - Organometallics

IS - 5

ER -

Organolanthanide-catalyzed cyclodimerizations of disubstituted alkynes

Abstract

Access to Document

Fingerprint

Research output

GMP Compliant Synthesis of Canagliflozin, a Novel PET Tracer for the Sodium−Glucose Cotransporter 2

Cite this