Addition reactions of η3-allenyl/propargyl and η3-trimethylenemethane complexes of platinum and palladium

Dunsizer, R.Todd; Marsico, Vera M; Plantevin, Véronique; Wojcicki, Andrew

doi:10.1016/s0020-1693(02)01168-4

Cited by 8 publications

(13 citation statements)

References 28 publications

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“…Further purification was achieved by dissolution in hexane and filtration through a plug of grade III deactivated alumina using first hexane and then hexane/CH 2 Cl 2 as the eluent. Yields of (g 5 -C 5 (Me)(CO 2 Me)(OEt)(Ph)H) Re(CO) 3 (2a) were typically higher than 0.26 g (ca. 90%).…”

Section: 3mentioning

confidence: 99%

“…IR and NMR spectra were obtained as reported earlier [2,3]. Mass spectra were recorded on a Kratos VG70-250S spectrometer by using either electron impact (EI) or fast atom bombardment (FAB) techniques.…”

Section: General Procedures and Measurementsmentioning

confidence: 99%

“…IR (hexane): m(CO) 2025 (m), 1945 (s), 1729 (w) cm À1 . 1 H NMR (CDCl 3 ): d 7.7-7.1 (m, 5H, Ph), 5.29 (s, 1H, CH), 3.87 (s, 3H, CO 2 Me), 3.80 (m, 2H, CH 2 Me), 2.49 (s, 3H, CMe), 1.25 (t, 3 J ¼ 7:0 Hz, 3H, OCH 2 Me). 13 Alternatively, 2a was prepared from 1a (0.300 g, 0.662 mmol) and PhCBCH (0.075 ml, 0.068 g) in 1.5 ml of toluene in a sealed tube heated at 120°C overnight.…”

Section: 3mentioning

confidence: 99%

“…Synthesis of (g 5 -C 5 (Me)(CO 2 Me)(OEt)(Ph)-(Ph))Re(CO) 3 (2d) from (CO) 4 Re(g 2 -C(Me)C(CO 2 -Me)C(OEt)) (1a) and PhCBCPh A solution of 1a (0.100 g, 0.221 mmol) in 10 ml of toluene was treated with 1 equivalent of PhCB CPh (0.040 g), and the mixutre was heated at reflux temperature for 3 h. The workup procedure followed that given in Section 2.3.1. After chromatography on grade III alumina with CH 2 Cl 2 /hexane as the eluent, 0.107 g (80%) of (g 5 -C 5 (Me)(CO 2 Me)(OEt)(Ph)(Ph))-Re(CO) 3 Complex 2d was also prepared by irradiating a solution of 1a and PhCBCPh (1 equivalent) in hexane. After ca.…”

Section: 3mentioning

confidence: 99%

“…Also presented were a number of reactions of 1, viz., deprotonation followed by alkylation at R (R ¼ alkyl), aminolysis at C(OR 0 ), nucleophilic addition (at C(R)) and substitution (at Re) by tertiary phosphine, and insertion of oxygen atom and the isoelectronic NH fragment into the Re@C bonds [1]. This paper focuses on additional chemistry of 1 and derivatives, including reactions with alkynes to yield tetra-and pentasubstituted g 5 -cyclopentadienylrhenium complexes (Cp z Re (CO) 3 (2)) and with sulfonium ylides to give nucleophilic addition at C(R) followed by rearrangement, as well as rearrangements induced by nitriles and pyridine.…”

Section: Introductionmentioning

confidence: 99%

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Chemistry of Fischer-type rhenacyclobutadiene complexes. II. Reactions with alkynes and sulfonium ylides, and rearrangements induced by nitriles and pyridine

Plantevin

Wojcicki

2004

Journal of Organometallic Chemistry

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Section: 3mentioning

confidence: 99%

Section: General Procedures and Measurementsmentioning

confidence: 99%

Section: 3mentioning

confidence: 99%

Section: 3mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Chemistry of Fischer-type rhenacyclobutadiene complexes. II. Reactions with alkynes and sulfonium ylides, and rearrangements induced by nitriles and pyridine

Plantevin

Wojcicki

2004

Journal of Organometallic Chemistry

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Platinum‐Catalyzed Friedel–Crafts‐Type C−H Coupling–Allylic Amination Cascade to Synthesize 3,4‐Fused Tricyclic Indoles

Suzuki

Tanaka

Nakano

et al. 2016

Chemistry A European J

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A novel platinum-catalyzed cascade cyclization reaction was developed by intramolecular Friedel-Crafts-type C-H coupling of aniline derivatives with a propargyl carbonate unit-allylic amination sequence. Treatment of various propargyl carbonates tethered to meta-aniline derivatives with a Pt(dba)3/DPEphos catalyst system afforded the corresponding 3,4-fused tricyclic 3-alkylidene indolines in 42-99% yield, which were transformed into 3,4-fused indole derivatives by reaction with trifluoroacetic acid. The reaction products exhibited antiproliferative activities against cancer cells, but not normal cells, revealing the potential usefulness of this reaction for medicinal chemistry.

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Mono‐ or Diplatinum Complexes Containing a π‐Conjugated Pentadiynyl Ligand

et al. 2010

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The reaction of pentadiynyl halides XCH2C≡CC≡CPh (1) with equimolar amounts of Pt(C2H4)(PPh3)2 in C6D6 produced cis‐(PPh3)2PtX(η1‐CH2C≡CC≡CPh) (cis‐2) as a kinetic product. Complex cis‐2 isomerized to trans‐(PPh3)2PtX(η1‐CH2C≡CC≡CPh) (trans‐2) or trans‐(PPh3)2PtX[η1‐C(C≡CPh)=C=CH2] (trans‐3) under some reaction conditions. In contrast to the reaction of Pt(C2H4)(PPh3)2, treatment of 1 with Pt(PPh3)4 generated cationic platinacyclobutene [(PPh3)2Pt{η2‐CH2C(PPh3)=C(C≡CPh)}]+Cl– (5) together with cis‐2 and trans‐2. Moreover, 2 equiv. of Pt(C2H4)(PPh3)2 and 1 provided η1,η2‐coordinated diplatinum complex cis‐(PPh3)2PtCl[η1‐ CH2C≡C{(PPh3)2Pt(η2‐C≡CPh)}] (7) and/or metallacyclobutene diplatinum complex (PPh3)2Pt[η2‐CH2C{(PPh3)2PtCl}=C(C≡CPh)] (8). The coordination modes of these complexes depend on the ratio of pentadiynyl halide, Pt, and PPh3, as well as temperature and the nature of the solvents. Protonolysis of metallacyclobutene complexes 5 and 8 with HCl gave [cis‐(PPh3)2PtCl{η1‐C(C≡CPh)=C(PPh3)CH3}]+Cl– (9) and [(PPh3)2Pt{η3‐CH2{cis‐(PPh3)2PtCl}CCH(C≡CPh)}]+Cl– (10). Single‐crystal X‐ray diffraction analysis of 12 showed η3‐ and η1‐coordination structure.

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Addition reactions of η3-allenyl/propargyl and η3-trimethylenemethane complexes of platinum and palladium

Cited by 8 publications

References 28 publications

Chemistry of Fischer-type rhenacyclobutadiene complexes. II. Reactions with alkynes and sulfonium ylides, and rearrangements induced by nitriles and pyridine

Chemistry of Fischer-type rhenacyclobutadiene complexes. II. Reactions with alkynes and sulfonium ylides, and rearrangements induced by nitriles and pyridine

Platinum‐Catalyzed Friedel–Crafts‐Type C−H Coupling–Allylic Amination Cascade to Synthesize 3,4‐Fused Tricyclic Indoles

Mono‐ or Diplatinum Complexes Containing a π‐Conjugated Pentadiynyl Ligand

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