M10: New Synthetic Methods II

What does Schwartz’s Reagent look like?

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What is it used for?

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Hydrozirconation

Schwartz reagent + alkene/alkyne

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1. Co-ordination

2. Hydrometallation

3. Zr-C bond is like a Grignard

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(Cp2Zr prefers to be terminal so will move a bond via beta H elimination + hydrozirconation)

(with alkynes, trans alkene formed due to syn addition step)

Carboalumination Catalysts

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(requires a Lewis Acid too!)

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(what is this reagent similar to?)

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Carboalumination

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(of alkynes)

Adds Me and AlMe2 syn across an alkyne
Carbocupration Catalyst
R-CuMgX2
Cobalt Catalyst

Co2(CO)8 -; Co2(CO)6

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Complexes with alkynes

Forms stable cation alpha to the alkyne

Pauson Khand

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[2+2+1]

cycloaddition

[image]

Nozaki-Hiyami-Kishi

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(like a Grignard)

2 Cr(II)Cl2 + Ni(II)Cl2 -; 2 Cr(III)Cl3 + Ni(0)

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C=C-X + Aldehyde

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Won’t react with ketone whereas Grignard will!

Nozaki-Hiyama-Kishi

 

Mechanism

[image]
Ti Carbene
Ti(Cp2)=
Tebbe Reagent
[image]
Petasis Reagent
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