Palladium iminoacyl imine complexes:  Strategies toward imine n insertion

Gareth R. Owen; Andrew J.P. White; Ramon Vilar

doi:10.1021/om900574b

Palladium iminoacyl imine complexes: Strategies toward imine n insertion

Gareth R. Owen, Andrew J.P. White, Ramon Vilar

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Abstract

The syntheses and characterization of a number of palladium complexes containing imine and/or iminoacyl groups are reported. Our strategies toward the insertion of imines into palladium iminoacyl complexes are outlined. The imine complexes [Pd(Me)(L₂){ N(R^')=C(H)Ph}]X (where L ₂ = dppe, dppp, dppf; R^' = Ph, Me, Bz; and X = BF ₄ or OTf) were prepared and fully characterized. [Pd(Me)(dppe){N(Ph)= C(H)Ph}]BF₄ (1) and [Pd(Me)(dppp){N(Ph)=C(H)Ph}]OTf (4) were structurally characterized by X-ray crystallography. The iminoacyl-imine complexes [Pd{C(Me)=NXyl} (L₂){N=C(Me)OCH₂CH ₂}]BF₄ (L₂ = dppe, 12; dppp, 13) were prepared. The bis-imine complex [Pd(dppe){N=C(Me)OCH₂CH₂} ₂][BF₄]₂ (14) resulting from disproportionation of 12 was also prepared and structurally characterized. Protonation of the iminoacyl fragment provided iminoacyl imine complex [Pd{C(CH₃)=N(H) Xyl}(dppe){N(Bz)=CPhH}][BF₄]₂ (17), which was sufficiently stable to be structurally characterized, providing some insight into the coordination of these fragments to palladium.

Original language	English
Pages (from-to)	5786-5793
Number of pages	8
Journal	Organometallics
Volume	28
Issue number	19
DOIs	https://doi.org/10.1021/om900574b
Publication status	Published - 12 Oct 2009
Externally published	Yes

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@article{bbf792d291764b83ac9d85d5322ee205,

title = "Palladium iminoacyl imine complexes: Strategies toward imine n insertion",

abstract = "The syntheses and characterization of a number of palladium complexes containing imine and/or iminoacyl groups are reported. Our strategies toward the insertion of imines into palladium iminoacyl complexes are outlined. The imine complexes [Pd(Me)(L2){ N(R')=C(H)Ph}]X (where L 2 = dppe, dppp, dppf; R' = Ph, Me, Bz; and X = BF 4 or OTf) were prepared and fully characterized. [Pd(Me)(dppe){N(Ph)= C(H)Ph}]BF4 (1) and [Pd(Me)(dppp){N(Ph)=C(H)Ph}]OTf (4) were structurally characterized by X-ray crystallography. The iminoacyl-imine complexes [Pd{C(Me)=NXyl} (L2){N=C(Me)OCH2CH 2}]BF4 (L2 = dppe, 12; dppp, 13) were prepared. The bis-imine complex [Pd(dppe){N=C(Me)OCH2CH2} 2][BF4]2 (14) resulting from disproportionation of 12 was also prepared and structurally characterized. Protonation of the iminoacyl fragment provided iminoacyl imine complex [Pd{C(CH3)=N(H) Xyl}(dppe){N(Bz)=CPhH}][BF4]2 (17), which was sufficiently stable to be structurally characterized, providing some insight into the coordination of these fragments to palladium.",

author = "Owen, {Gareth R.} and White, {Andrew J.P.} and Ramon Vilar",

year = "2009",

month = oct,

day = "12",

doi = "10.1021/om900574b",

language = "English",

volume = "28",

pages = "5786--5793",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Palladium iminoacyl imine complexes

T2 - Strategies toward imine n insertion

AU - Owen, Gareth R.

AU - White, Andrew J.P.

AU - Vilar, Ramon

PY - 2009/10/12

Y1 - 2009/10/12

N2 - The syntheses and characterization of a number of palladium complexes containing imine and/or iminoacyl groups are reported. Our strategies toward the insertion of imines into palladium iminoacyl complexes are outlined. The imine complexes [Pd(Me)(L2){ N(R')=C(H)Ph}]X (where L 2 = dppe, dppp, dppf; R' = Ph, Me, Bz; and X = BF 4 or OTf) were prepared and fully characterized. [Pd(Me)(dppe){N(Ph)= C(H)Ph}]BF4 (1) and [Pd(Me)(dppp){N(Ph)=C(H)Ph}]OTf (4) were structurally characterized by X-ray crystallography. The iminoacyl-imine complexes [Pd{C(Me)=NXyl} (L2){N=C(Me)OCH2CH 2}]BF4 (L2 = dppe, 12; dppp, 13) were prepared. The bis-imine complex [Pd(dppe){N=C(Me)OCH2CH2} 2][BF4]2 (14) resulting from disproportionation of 12 was also prepared and structurally characterized. Protonation of the iminoacyl fragment provided iminoacyl imine complex [Pd{C(CH3)=N(H) Xyl}(dppe){N(Bz)=CPhH}][BF4]2 (17), which was sufficiently stable to be structurally characterized, providing some insight into the coordination of these fragments to palladium.

AB - The syntheses and characterization of a number of palladium complexes containing imine and/or iminoacyl groups are reported. Our strategies toward the insertion of imines into palladium iminoacyl complexes are outlined. The imine complexes [Pd(Me)(L2){ N(R')=C(H)Ph}]X (where L 2 = dppe, dppp, dppf; R' = Ph, Me, Bz; and X = BF 4 or OTf) were prepared and fully characterized. [Pd(Me)(dppe){N(Ph)= C(H)Ph}]BF4 (1) and [Pd(Me)(dppp){N(Ph)=C(H)Ph}]OTf (4) were structurally characterized by X-ray crystallography. The iminoacyl-imine complexes [Pd{C(Me)=NXyl} (L2){N=C(Me)OCH2CH 2}]BF4 (L2 = dppe, 12; dppp, 13) were prepared. The bis-imine complex [Pd(dppe){N=C(Me)OCH2CH2} 2][BF4]2 (14) resulting from disproportionation of 12 was also prepared and structurally characterized. Protonation of the iminoacyl fragment provided iminoacyl imine complex [Pd{C(CH3)=N(H) Xyl}(dppe){N(Bz)=CPhH}][BF4]2 (17), which was sufficiently stable to be structurally characterized, providing some insight into the coordination of these fragments to palladium.

U2 - 10.1021/om900574b

DO - 10.1021/om900574b

M3 - Article

AN - SCOPUS:70349759670

SN - 0276-7333

VL - 28

SP - 5786

EP - 5793

JO - Organometallics

JF - Organometallics

IS - 19

ER -

Palladium iminoacyl imine complexes: Strategies toward imine n insertion

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