Reactions of ruthenium(o) phosphine complexes with diphenylacetylene

Anthony F. Hill; Madeleine Schultz; Anthony C. Willis

doi:10.1021/om0400954

Reactions of ruthenium(o) phosphine complexes with diphenylacetylene

Anthony F. Hill^*, Madeleine Schultz, Anthony C. Willis

^*Corresponding author for this work

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

25 Citations (Scopus)

Abstract

Heating diphenylacetylene with [Ru(CO)₂(PPh₃) ₃] in toluene under reflux provides the 2-phenylindenone complex [Ru(η³=CCPh=CHC₆H₄)(CO)(PPh ₃)₂], arising from C-H activation of one ortho-proton of diphenylacetylene, hydroruthenation of the triple bond, and cyclization incorporating one carbonyl ligand. Both phosphines are replaced by 1,2-bis-(diphenylphosphino)ethane to provide [Ru(η⁴-O=CCPh= CHC₆H₄)(CO)(dppe)]. In contrast, heating diphenylacetylene with [Ru(CO)₃(PPh₃)₂] in toluene under reflux generates the tetraphenylcyclopentadienone complex [Ru(η⁴-C)= CC₄Ph₄)(CO)₂(PPh₃)] in high yield, via [2+2+1] alkyne and CO cyclization. The crystal structures of [Ru(η⁴4-O=CCPh=CHC₆H₄)-(CO)(PPh ₃)₂], [Ru(η⁴-O=CCPh=CHC₆H ₄)(CO)(dppe)], [Ru(η⁴-O=CC₄Ph ₄)(CO)₂(PPh₃)], and [Ru(η-PhC=CPh)(CO) ₂(PPh₃)₂] solvates are reported.

Original language	English
Pages (from-to)	5729-5736
Number of pages	8
Journal	Organometallics
Volume	23
Issue number	24
DOIs	https://doi.org/10.1021/om0400954
Publication status	Published - 22 Nov 2004

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@article{b9c1fafe7c7e4d4b83514ebd4fab62c7,

title = "Reactions of ruthenium(o) phosphine complexes with diphenylacetylene",

abstract = "Heating diphenylacetylene with [Ru(CO)2(PPh3) 3] in toluene under reflux provides the 2-phenylindenone complex [Ru(η3=CCPh=CHC6H4)(CO)(PPh 3)2], arising from C-H activation of one ortho-proton of diphenylacetylene, hydroruthenation of the triple bond, and cyclization incorporating one carbonyl ligand. Both phosphines are replaced by 1,2-bis-(diphenylphosphino)ethane to provide [Ru(η4-O=CCPh= CHC6H4)(CO)(dppe)]. In contrast, heating diphenylacetylene with [Ru(CO)3(PPh3)2] in toluene under reflux generates the tetraphenylcyclopentadienone complex [Ru(η4-C)= CC4Ph4)(CO)2(PPh3)] in high yield, via [2+2+1] alkyne and CO cyclization. The crystal structures of [Ru(η44-O=CCPh=CHC6H4)-(CO)(PPh 3)2], [Ru(η4-O=CCPh=CHC6H 4)(CO)(dppe)], [Ru(η4-O=CC4Ph 4)(CO)2(PPh3)], and [Ru(η-PhC=CPh)(CO) 2(PPh3)2] solvates are reported.",

author = "Hill, {Anthony F.} and Madeleine Schultz and Willis, {Anthony C.}",

year = "2004",

month = nov,

day = "22",

doi = "10.1021/om0400954",

language = "English",

volume = "23",

pages = "5729--5736",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "24",

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TY - JOUR

T1 - Reactions of ruthenium(o) phosphine complexes with diphenylacetylene

AU - Hill, Anthony F.

AU - Schultz, Madeleine

AU - Willis, Anthony C.

PY - 2004/11/22

Y1 - 2004/11/22

N2 - Heating diphenylacetylene with [Ru(CO)2(PPh3) 3] in toluene under reflux provides the 2-phenylindenone complex [Ru(η3=CCPh=CHC6H4)(CO)(PPh 3)2], arising from C-H activation of one ortho-proton of diphenylacetylene, hydroruthenation of the triple bond, and cyclization incorporating one carbonyl ligand. Both phosphines are replaced by 1,2-bis-(diphenylphosphino)ethane to provide [Ru(η4-O=CCPh= CHC6H4)(CO)(dppe)]. In contrast, heating diphenylacetylene with [Ru(CO)3(PPh3)2] in toluene under reflux generates the tetraphenylcyclopentadienone complex [Ru(η4-C)= CC4Ph4)(CO)2(PPh3)] in high yield, via [2+2+1] alkyne and CO cyclization. The crystal structures of [Ru(η44-O=CCPh=CHC6H4)-(CO)(PPh 3)2], [Ru(η4-O=CCPh=CHC6H 4)(CO)(dppe)], [Ru(η4-O=CC4Ph 4)(CO)2(PPh3)], and [Ru(η-PhC=CPh)(CO) 2(PPh3)2] solvates are reported.

AB - Heating diphenylacetylene with [Ru(CO)2(PPh3) 3] in toluene under reflux provides the 2-phenylindenone complex [Ru(η3=CCPh=CHC6H4)(CO)(PPh 3)2], arising from C-H activation of one ortho-proton of diphenylacetylene, hydroruthenation of the triple bond, and cyclization incorporating one carbonyl ligand. Both phosphines are replaced by 1,2-bis-(diphenylphosphino)ethane to provide [Ru(η4-O=CCPh= CHC6H4)(CO)(dppe)]. In contrast, heating diphenylacetylene with [Ru(CO)3(PPh3)2] in toluene under reflux generates the tetraphenylcyclopentadienone complex [Ru(η4-C)= CC4Ph4)(CO)2(PPh3)] in high yield, via [2+2+1] alkyne and CO cyclization. The crystal structures of [Ru(η44-O=CCPh=CHC6H4)-(CO)(PPh 3)2], [Ru(η4-O=CCPh=CHC6H 4)(CO)(dppe)], [Ru(η4-O=CC4Ph 4)(CO)2(PPh3)], and [Ru(η-PhC=CPh)(CO) 2(PPh3)2] solvates are reported.

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U2 - 10.1021/om0400954

DO - 10.1021/om0400954

M3 - Article

SN - 0276-7333

VL - 23

SP - 5729

EP - 5736

JO - Organometallics

JF - Organometallics

IS - 24

ER -

Reactions of ruthenium(o) phosphine complexes with diphenylacetylene

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