New approach to chiral phosphapalladacycles: first optically active phosphinite PC-palladacycle with non-metallocenic planar chirality

Dunina, V. V.; Turubanova, Eugeniya I.; Ливанцов, М. В.; Grishin, Yuri K.

doi:10.1016/j.tetasy.2008.06.032

Cited by 21 publications

(11 citation statements)

References 30 publications

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“…Heating of each of the diastereomers, (RPl,RC)-5-8 and (SPl,RC)-5-8, afforded two enantiomers of the target dimers 5-9, (SPl,SPl) and (RPl,RPl), in ca. 50% yields [35]. Chiral primary amine complex 5-1 is stereochemically advantageous compared to other chiral palladacycles.…”

Section: Asymmetric Version Of the Ligand Exchangementioning

confidence: 98%

“…Heating of each of the diastereomers, (R Pl ,R C )-5-8 and (S Pl ,R C )-5-8, afforded two enantiomers of the target dimers 5-9, (S Pl ,S Pl ) and (R Pl ,R Pl ), in ca. 50% yields [35].…”

Section: Scheme 9 the Exchange Between Chiral 5-1 With A Primary Amimentioning

confidence: 99%

“…T of the exchange was performed in toluene in the presence of glacial acetic a of each of the diastereomers, (RPl,RC)-5-8 and (SPl,RC)-5-8, afforded two enant target dimers 5-9, (SPl,SPl) and (RPl,RPl), in ca. 50% yields[35].…”

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confidence: 99%

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The Exchange of Cyclometalated Ligands

Ryabov

2021

Molecules

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Reactions of cyclometalated compounds are numerous. This account is focused on one of such reactions, the exchange of cyclometalated ligands, a reaction between a cyclometalated compound and an incoming ligand that replaces a previously cyclometalated ligand to form a new metalacycle: + H-C*~Z ⇄ + H-C~Y. Originally discovered for PdII complexes with Y/Z = N, P, S, the exchange appeared to be a mechanistically challenging, simple, and convenient routine for the synthesis of cyclopalladated complexes. Over four decades it was expanded to cyclometalated derivatives of platinum, ruthenium, manganese, rhodium, and iridium. The exchange, which is also questionably referred to as transcyclometalation, offers attractive synthetic possibilities and assists in disclosing key mechanistic pathways associated with the C–H bond activation by transition metal complexes and C–M bond cleavage. Both synthetic and mechanistic aspects of the exchange are reviewed and discussed.

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Section: Asymmetric Version Of the Ligand Exchangementioning

confidence: 98%

“…Heating of each of the diastereomers, (R Pl ,R C )-5-8 and (S Pl ,R C )-5-8, afforded two enantiomers of the target dimers 5-9, (S Pl ,S Pl ) and (R Pl ,R Pl ), in ca. 50% yields [35].…”

Section: Scheme 9 the Exchange Between Chiral 5-1 With A Primary Amimentioning

confidence: 99%

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The Exchange of Cyclometalated Ligands

Ryabov

2021

Molecules

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“…Monophosphinite 90 has been prepared in enantiopure form from 4‐hydroxy[2.2]paracyclophane 61. Alternatively, racemic 90 has been used to synthesise an enantiopure planar chiral palladacycle 92 (Scheme ) 64. The most efficient route involved complexation of the phosphinite (±)‐90 with a chiral palladacycle to give the diastereomeric complexes 91 .…”

Section: Monophosphinesmentioning

confidence: 99%

Planar Chiral Phosphines Derived from [2.2]Paracyclophane

Rowlands

2012

Israel Journal of Chemistry

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radicals and, of course, the chemistry of [2.2]paracyclophane. He lives with his partner, Kate, two insane cats and an ever growing pile of cds and books that he has no hope of ever finishing. Scheme 2. Reduction of a tetrahydropyrazine. Reaction conditions: (a) 12 a (2 mol %), H 2 (1.5 atm), À40 8C, 6 h, > 99 %, 86 % ee. The absolute stereochemistry of 14 is not given in ref. [6]. Scheme 3. Synthesis of diaryl amino acid. Reaction conditions: (a) [(R)-12 a-Rh(cod)]BF 4 (0.4 mol %), H 2 (10 atm), rt, > 99 %, 89 % ee.

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“…For background to palladium compounds in catalysis, see: Dunina et al (2008Dunina et al ( , 2009; Bedford et al (2004); Morales-Morales et al (2002). For the synthesis of the starting materials, see: Drew & Doyle (1990).…”

Section: Related Literaturementioning

confidence: 99%

Di-μ-chlorido-bis({8-[bis(naphthalen-1-yl)phosphanyl]naphthalen-1-yl-κ²C¹,P}palladium(II)) dichloromethane disolvate

Davis

Muller

2012

Acta Cryst E

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The title compound, [Pd2{P(C10H7)2(C10H6)}2Cl2]·2CH2Cl2, shows cyclometalation of one naphthalen-1-yl substituent of each of the phosphane ligands to the Pd dimer in a trans orientation; the complete dimer is generated by a centre of inversion. Two dichloromethane solvent molecules create C—H⋯Cl interactions with the metal complex, generating supermolecular layers in the ab plane. Additional C—H⋯π and π–π [centroid–centroid distances = 3.713 (3), 3.850 (4) and 3.926 (3) Å] interactions join these planes into a three-dimensional supermolecular network.

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New approach to chiral phosphapalladacycles: first optically active phosphinite PC-palladacycle with non-metallocenic planar chirality

Cited by 21 publications

References 30 publications

The Exchange of Cyclometalated Ligands

The Exchange of Cyclometalated Ligands

Planar Chiral Phosphines Derived from [2.2]Paracyclophane

Di-μ-chlorido-bis({8-[bis(naphthalen-1-yl)phosphanyl]naphthalen-1-yl-κ²C¹,P}palladium(II)) dichloromethane disolvate

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New approach to chiral phosphapalladacycles: first optically active phosphinite PC-palladacycle with non-metallocenic planar chirality

Cited by 21 publications

References 30 publications

The Exchange of Cyclometalated Ligands

The Exchange of Cyclometalated Ligands

Planar Chiral Phosphines Derived from [2.2]Paracyclophane

Di-μ-chlorido-bis({8-[bis(naphthalen-1-yl)phosphanyl]naphthalen-1-yl-κ2C1,P}palladium(II)) dichloromethane disolvate

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Di-μ-chlorido-bis({8-[bis(naphthalen-1-yl)phosphanyl]naphthalen-1-yl-κ²C¹,P}palladium(II)) dichloromethane disolvate