Unprecedented ROMP Activity of Low-Valent Rhenium-Nitrosyl Complexes: Mechanistic Evaluation of an Electrophilic Olefin Metathesis System

The reaction of [Re(H)(NO)2(PR3)2] complexes (1 a: R = PCy3; 1 b: R = PiPr3) with [H(OEt2)2][BArF4] ([BArF4] = tetrakis{3,5‐bis(trifluoromethyl)phenyl}borate) in benzene at room temperature gave the corresponding cations [Re(NO)2(PR3)2][BArF4] (2 a and 2 b). The addition of phenyldiazomethane to ben...

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Vydané v:Chemistry : a European journal Ročník 12; číslo 12; s. 3325 - 3338
Hlavní autori: Frech, Christian M., Blacque, Olivier, Schmalle, Helmut W., Berke, Heinz, Adlhart, Christian, Chen, Peter
Médium: Journal Article
Jazyk:English
Vydavateľské údaje: Weinheim WILEY-VCH Verlag 12.04.2006
WILEY‐VCH Verlag
Predmet:
density functional calculations
metathesis
reaction mechanisms
rhenium
ring- opening polymerization
ISSN:0947-6539, 1521-3765
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Abstract The reaction of [Re(H)(NO)2(PR3)2] complexes (1 a: R = PCy3; 1 b: R = PiPr3) with [H(OEt2)2][BArF4] ([BArF4] = tetrakis{3,5‐bis(trifluoromethyl)phenyl}borate) in benzene at room temperature gave the corresponding cations [Re(NO)2(PR3)2][BArF4] (2 a and 2 b). The addition of phenyldiazomethane to benzene solutions of 2 a and 2 b afforded the moderately stable cationic rhenium(I)‐benzylidene‐dinitrosyl‐bis(trialkyl)phosphine complexes 3 a and 3 b as [BArF4]− salts in good yields. The complexes 2 a and 2 b catalyze the ring‐opening metathesis polymerization (ROMP) of highly strained nonfunctionalized cyclic olefins to give polymers with relatively high polydispersity indices, high molecular weights and over 80 % Z configuration of the double bonds in the chain backbone. However, these complexes do not show metathesis activity with acyclic olefins. The benzylidene derivatives 3 a and 3 b are almost inactive in ROMP catalysis with norbornene and in olefin metathesis. NMR experiments gave the first hints of the initial formation of carbene complexes from [Re(NO)2(PR3)2][BArF4] (2 a and 2 b) and norbornene. In a detailed mechanistic study ESI‐MS/MS measurements provided further evidence that the carbene formation is initiated by a unique reaction sequence where the cleavage of the strained olefinic bond starts with phosphine migration forming a cyclic ylide–carbene complex, capable of undergoing metathesis with alternating rhenacyclobutane formation and cycloreversion reactions (“ylide” route). However, even at an early stage the ROMP propagation route is expected to merge into an “iminate” route by attack by the ylide function on one of the NNO atoms followed by phosphine oxide elimination. The formation of phosphine oxide was confirmed by NMR spectroscopy. The proposed mechanism is supported further by detailed DFT calculations. A unique catalytic mechanism operates as illustrated to form the initiating carbene complex when stable low‐valent [Re(NO)2(PR3)2]+ cations catalyze the unprecedented ROMP of strained nonfunctionalized olefins. This yields high‐molecular‐weight polymers with predominantly Z‐olefinic content.
AbstractList The reaction of [Re(H)(NO)2(PR3)2] complexes (1 a: R = PCy3; 1 b: R = PiPr3) with [H(OEt2)2][BAr(F)4] ([BAr(F)4] = tetrakis{3,5-bis(trifluoromethyl)phenyl}borate) in benzene at room temperature gave the corresponding cations [Re(NO)2(PR3)2][BAr(F)4] (2 a and 2 b). The addition of phenyldiazomethane to benzene solutions of 2 a and 2 b afforded the moderately stable cationic rhenium(I)-benzylidene-dinitrosyl-bis(trialkyl)phosphine complexes 3 a and 3 b as [BAr(F)4]- salts in good yields. The complexes 2 a and 2 b catalyze the ring-opening metathesis polymerization (ROMP) of highly strained nonfunctionalized cyclic olefins to give polymers with relatively high polydispersity indices, high molecular weights and over 80 % Z configuration of the double bonds in the chain backbone. However, these complexes do not show metathesis activity with acyclic olefins. The benzylidene derivatives 3 a and 3 b are almost inactive in ROMP catalysis with norbornene and in olefin metathesis. NMR experiments gave the first hints of the initial formation of carbene complexes from [Re(NO)2(PR3)2][BAr(F)4] (2 a and 2 b) and norbornene. In a detailed mechanistic study ESI-MS/MS measurements provided further evidence that the carbene formation is initiated by a unique reaction sequence where the cleavage of the strained olefinic bond starts with phosphine migration forming a cyclic ylide-carbene complex, capable of undergoing metathesis with alternating rhenacyclobutane formation and cycloreversion reactions ("ylide" route). However, even at an early stage the ROMP propagation route is expected to merge into an "iminate" route by attack by the ylide function on one of the N(NO) atoms followed by phosphine oxide elimination. The formation of phosphine oxide was confirmed by NMR spectroscopy. The proposed mechanism is supported further by detailed DFT calculations.
The reaction of [Re(H)(NO)2(PR3)2] complexes (1 a: R = PCy3; 1 b: R = PiPr3) with [H(OEt2)2][BArF4] ([BArF4] = tetrakis{3,5‐bis(trifluoromethyl)phenyl}borate) in benzene at room temperature gave the corresponding cations [Re(NO)2(PR3)2][BArF4] (2 a and 2 b). The addition of phenyldiazomethane to benzene solutions of 2 a and 2 b afforded the moderately stable cationic rhenium(I)‐benzylidene‐dinitrosyl‐bis(trialkyl)phosphine complexes 3 a and 3 b as [BArF4]− salts in good yields. The complexes 2 a and 2 b catalyze the ring‐opening metathesis polymerization (ROMP) of highly strained nonfunctionalized cyclic olefins to give polymers with relatively high polydispersity indices, high molecular weights and over 80 % Z configuration of the double bonds in the chain backbone. However, these complexes do not show metathesis activity with acyclic olefins. The benzylidene derivatives 3 a and 3 b are almost inactive in ROMP catalysis with norbornene and in olefin metathesis. NMR experiments gave the first hints of the initial formation of carbene complexes from [Re(NO)2(PR3)2][BArF4] (2 a and 2 b) and norbornene. In a detailed mechanistic study ESI‐MS/MS measurements provided further evidence that the carbene formation is initiated by a unique reaction sequence where the cleavage of the strained olefinic bond starts with phosphine migration forming a cyclic ylide–carbene complex, capable of undergoing metathesis with alternating rhenacyclobutane formation and cycloreversion reactions (“ylide” route). However, even at an early stage the ROMP propagation route is expected to merge into an “iminate” route by attack by the ylide function on one of the NNO atoms followed by phosphine oxide elimination. The formation of phosphine oxide was confirmed by NMR spectroscopy. The proposed mechanism is supported further by detailed DFT calculations. A unique catalytic mechanism operates as illustrated to form the initiating carbene complex when stable low‐valent [Re(NO)2(PR3)2]+ cations catalyze the unprecedented ROMP of strained nonfunctionalized olefins. This yields high‐molecular‐weight polymers with predominantly Z‐olefinic content.
The reaction of [Re(H)(NO) 2 (PR 3 ) 2 ] complexes ( 1 a : R = PCy 3 ; 1 b : R = P i Pr 3 ) with [H(OEt 2 ) 2 ][BAr F 4 ] ([BAr F 4 ] = tetrakis{3,5‐bis(trifluoromethyl)phenyl}borate) in benzene at room temperature gave the corresponding cations [Re(NO) 2 (PR 3 ) 2 ][BAr F 4 ] ( 2 a and 2 b ). The addition of phenyldiazomethane to benzene solutions of 2 a and 2 b afforded the moderately stable cationic rhenium( I )‐benzylidene‐dinitrosyl‐bis(trialkyl)phosphine complexes 3 a and 3 b as [BAr F 4 ] − salts in good yields. The complexes 2 a and 2 b catalyze the ring‐opening metathesis polymerization (ROMP) of highly strained nonfunctionalized cyclic olefins to give polymers with relatively high polydispersity indices, high molecular weights and over 80 % Z configuration of the double bonds in the chain backbone. However, these complexes do not show metathesis activity with acyclic olefins. The benzylidene derivatives 3 a and 3 b are almost inactive in ROMP catalysis with norbornene and in olefin metathesis. NMR experiments gave the first hints of the initial formation of carbene complexes from [Re(NO) 2 (PR 3 ) 2 ][BAr F 4 ] ( 2 a and 2 b ) and norbornene. In a detailed mechanistic study ESI‐MS/MS measurements provided further evidence that the carbene formation is initiated by a unique reaction sequence where the cleavage of the strained olefinic bond starts with phosphine migration forming a cyclic ylide–carbene complex, capable of undergoing metathesis with alternating rhenacyclobutane formation and cycloreversion reactions (“ylide” route). However, even at an early stage the ROMP propagation route is expected to merge into an “iminate” route by attack by the ylide function on one of the N NO atoms followed by phosphine oxide elimination. The formation of phosphine oxide was confirmed by NMR spectroscopy. The proposed mechanism is supported further by detailed DFT calculations.
The reaction of [Re(H)(NO)2(PR3)2] complexes (1 a: R = PCy3; 1 b: R = PiPr3) with [H(OEt2)2][BAr(F)4] ([BAr(F)4] = tetrakis{3,5-bis(trifluoromethyl)phenyl}borate) in benzene at room temperature gave the corresponding cations [Re(NO)2(PR3)2][BAr(F)4] (2 a and 2 b). The addition of phenyldiazomethane to benzene solutions of 2 a and 2 b afforded the moderately stable cationic rhenium(I)-benzylidene-dinitrosyl-bis(trialkyl)phosphine complexes 3 a and 3 b as [BAr(F)4]- salts in good yields. The complexes 2 a and 2 b catalyze the ring-opening metathesis polymerization (ROMP) of highly strained nonfunctionalized cyclic olefins to give polymers with relatively high polydispersity indices, high molecular weights and over 80 % Z configuration of the double bonds in the chain backbone. However, these complexes do not show metathesis activity with acyclic olefins. The benzylidene derivatives 3 a and 3 b are almost inactive in ROMP catalysis with norbornene and in olefin metathesis. NMR experiments gave the first hints of the initial formation of carbene complexes from [Re(NO)2(PR3)2][BAr(F)4] (2 a and 2 b) and norbornene. In a detailed mechanistic study ESI-MS/MS measurements provided further evidence that the carbene formation is initiated by a unique reaction sequence where the cleavage of the strained olefinic bond starts with phosphine migration forming a cyclic ylide-carbene complex, capable of undergoing metathesis with alternating rhenacyclobutane formation and cycloreversion reactions ("ylide" route). However, even at an early stage the ROMP propagation route is expected to merge into an "iminate" route by attack by the ylide function on one of the N(NO) atoms followed by phosphine oxide elimination. The formation of phosphine oxide was confirmed by NMR spectroscopy. The proposed mechanism is supported further by detailed DFT calculations.The reaction of [Re(H)(NO)2(PR3)2] complexes (1 a: R = PCy3; 1 b: R = PiPr3) with [H(OEt2)2][BAr(F)4] ([BAr(F)4] = tetrakis{3,5-bis(trifluoromethyl)phenyl}borate) in benzene at room temperature gave the corresponding cations [Re(NO)2(PR3)2][BAr(F)4] (2 a and 2 b). The addition of phenyldiazomethane to benzene solutions of 2 a and 2 b afforded the moderately stable cationic rhenium(I)-benzylidene-dinitrosyl-bis(trialkyl)phosphine complexes 3 a and 3 b as [BAr(F)4]- salts in good yields. The complexes 2 a and 2 b catalyze the ring-opening metathesis polymerization (ROMP) of highly strained nonfunctionalized cyclic olefins to give polymers with relatively high polydispersity indices, high molecular weights and over 80 % Z configuration of the double bonds in the chain backbone. However, these complexes do not show metathesis activity with acyclic olefins. The benzylidene derivatives 3 a and 3 b are almost inactive in ROMP catalysis with norbornene and in olefin metathesis. NMR experiments gave the first hints of the initial formation of carbene complexes from [Re(NO)2(PR3)2][BAr(F)4] (2 a and 2 b) and norbornene. In a detailed mechanistic study ESI-MS/MS measurements provided further evidence that the carbene formation is initiated by a unique reaction sequence where the cleavage of the strained olefinic bond starts with phosphine migration forming a cyclic ylide-carbene complex, capable of undergoing metathesis with alternating rhenacyclobutane formation and cycloreversion reactions ("ylide" route). However, even at an early stage the ROMP propagation route is expected to merge into an "iminate" route by attack by the ylide function on one of the N(NO) atoms followed by phosphine oxide elimination. The formation of phosphine oxide was confirmed by NMR spectroscopy. The proposed mechanism is supported further by detailed DFT calculations.
Author Frech, Christian M.
Adlhart, Christian
Blacque, Olivier
Berke, Heinz
Schmalle, Helmut W.
Chen, Peter
Author_xml – sequence: 1
  givenname: Christian M.
  surname: Frech
  fullname: Frech, Christian M.
  organization: Department of Inorganic Chemistry, University of Zürich, 8057 Zürich, Switzerland, Fax: (+41) 44-635-6802
– sequence: 2
  givenname: Olivier
  surname: Blacque
  fullname: Blacque, Olivier
  organization: Department of Inorganic Chemistry, University of Zürich, 8057 Zürich, Switzerland, Fax: (+41) 44-635-6802
– sequence: 3
  givenname: Helmut W.
  surname: Schmalle
  fullname: Schmalle, Helmut W.
  organization: Department of Inorganic Chemistry, University of Zürich, 8057 Zürich, Switzerland, Fax: (+41) 44-635-6802
– sequence: 4
  givenname: Heinz
  surname: Berke
  fullname: Berke, Heinz
  email: hberke@aci.unizh.ch
  organization: Department of Inorganic Chemistry, University of Zürich, 8057 Zürich, Switzerland, Fax: (+41) 44-635-6802
– sequence: 5
  givenname: Christian
  surname: Adlhart
  fullname: Adlhart, Christian
  organization: Eidgenössische Technische Hochschule, Laboratorium für Organische Chemie, ETH Hönggerberg, 8093 Zürich, Switzerland
– sequence: 6
  givenname: Peter
  surname: Chen
  fullname: Chen, Peter
  organization: Eidgenössische Technische Hochschule, Laboratorium für Organische Chemie, ETH Hönggerberg, 8093 Zürich, Switzerland
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Snippet The reaction of [Re(H)(NO)2(PR3)2] complexes (1 a: R = PCy3; 1 b: R = PiPr3) with [H(OEt2)2][BArF4] ([BArF4] = tetrakis{3,5‐bis(trifluoromethyl)phenyl}borate)...
The reaction of [Re(H)(NO) 2 (PR 3 ) 2 ] complexes ( 1 a : R = PCy 3 ; 1 b : R = P i Pr 3 ) with [H(OEt 2 ) 2 ][BAr F 4 ] ([BAr F 4 ] =...
The reaction of [Re(H)(NO)2(PR3)2] complexes (1 a: R = PCy3; 1 b: R = PiPr3) with [H(OEt2)2][BAr(F)4] ([BAr(F)4] =...
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SubjectTerms density functional calculations
metathesis
reaction mechanisms
rhenium
ring- opening polymerization
Title Unprecedented ROMP Activity of Low-Valent Rhenium-Nitrosyl Complexes: Mechanistic Evaluation of an Electrophilic Olefin Metathesis System
URI https://api.istex.fr/ark:/67375/WNG-XV7949MR-G/fulltext.pdf
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Volume 12
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