Platinum catalysed hydrostannylation of terminal alkynes; highly selective synthesis of vinyl stannanes

Dean D. Roberts; Mark G. McLaughlin

doi:10.1002/adsc.202300379

Platinum catalysed hydrostannylation of terminal alkynes; highly selective synthesis of vinyl stannanes

Dean D. Roberts, Mark G. McLaughlin^*

^*Corresponding author for this work

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

4 Citations (Scopus)

40 Downloads (Pure)

Abstract

We present the first study on the application of platinum complexes in the hydrostannylation of terminal alkynes. A range of platinum complexes were screened, with PtCl2/XPhos proving to provide the best selectivity for the β-(E)-vinyl stannane. The catalyst system is able to provide the corresponding vinyl stannane in selectivities which surpasses that which is typically afforded under palladium catalysis. Additionally, a telescoped hydrometallation/cross-coupling sequence has been developed, allowing for application of the vinyl stannanes without excessive manipulation or purification of the intermediate stannane.

Original language	English
Pages (from-to)	1602-1606
Journal	Advanced Synthesis & Catalysis
Volume	365
Issue number	10
Early online date	16 May 2023
DOIs	https://doi.org/10.1002/adsc.202300379
Publication status	Published - 23 May 2023
Externally published	Yes

Access to Document

10.1002/adsc.202300379Licence: CC BY

Platinum catalysed hydrostannylation of terminal alkynes; highly selective synthesis of vinyl stannanes
Copyright 2023 the authors. This is an open access article published under a Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
Final published version, 4.03 MBLicence: CC BY

Cite this

@article{55690c9ad4a14771ad324018876dff07,

title = "Platinum catalysed hydrostannylation of terminal alkynes; highly selective synthesis of vinyl stannanes",

abstract = "We present the first study on the application of platinum complexes in the hydrostannylation of terminal alkynes. A range of platinum complexes were screened, with PtCl2/XPhos proving to provide the best selectivity for the β-(E)-vinyl stannane. The catalyst system is able to provide the corresponding vinyl stannane in selectivities which surpasses that which is typically afforded under palladium catalysis. Additionally, a telescoped hydrometallation/cross-coupling sequence has been developed, allowing for application of the vinyl stannanes without excessive manipulation or purification of the intermediate stannane.",

author = "Roberts, {Dean D.} and McLaughlin, {Mark G.}",

year = "2023",

month = may,

day = "23",

doi = "10.1002/adsc.202300379",

language = "English",

volume = "365",

pages = " 1602--1606",

journal = "Advanced Synthesis & Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "10",

}

TY - JOUR

T1 - Platinum catalysed hydrostannylation of terminal alkynes; highly selective synthesis of vinyl stannanes

AU - Roberts, Dean D.

AU - McLaughlin, Mark G.

PY - 2023/5/23

Y1 - 2023/5/23

N2 - We present the first study on the application of platinum complexes in the hydrostannylation of terminal alkynes. A range of platinum complexes were screened, with PtCl2/XPhos proving to provide the best selectivity for the β-(E)-vinyl stannane. The catalyst system is able to provide the corresponding vinyl stannane in selectivities which surpasses that which is typically afforded under palladium catalysis. Additionally, a telescoped hydrometallation/cross-coupling sequence has been developed, allowing for application of the vinyl stannanes without excessive manipulation or purification of the intermediate stannane.

AB - We present the first study on the application of platinum complexes in the hydrostannylation of terminal alkynes. A range of platinum complexes were screened, with PtCl2/XPhos proving to provide the best selectivity for the β-(E)-vinyl stannane. The catalyst system is able to provide the corresponding vinyl stannane in selectivities which surpasses that which is typically afforded under palladium catalysis. Additionally, a telescoped hydrometallation/cross-coupling sequence has been developed, allowing for application of the vinyl stannanes without excessive manipulation or purification of the intermediate stannane.

U2 - 10.1002/adsc.202300379

DO - 10.1002/adsc.202300379

M3 - Article

SN - 1615-4150

VL - 365

SP - 1602

EP - 1606

JO - Advanced Synthesis & Catalysis

JF - Advanced Synthesis & Catalysis

IS - 10

ER -

Platinum catalysed hydrostannylation of terminal alkynes; highly selective synthesis of vinyl stannanes

Abstract

Access to Document

Fingerprint

Cite this