Questions tagged [organotransition-metal-chemistry]

For questions about the use of transition metals in organic synthesis.

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20
votes
1answer
711 views

Carbometalation of alkenes

Alkynes are capable of undergoing carbometalation, e.g. with organocopper reagents: Why don't the corresponding alkenes undergo analogous carbometalation reactions? Is β-elimination the issue?
13
votes
1answer
177 views

Mechanism for palladium-catalysed spirocyclisation of conjugated diene

I'm trying to work out the catalytic cycle for the following process: I gather that the palladium will be reduced from Pd(II) to Pd(0) in the process and that the 1,4-benzoquinone is a redoxidant. ...
8
votes
2answers
777 views

Why is Ni[(PPh₃)₂Cl₂] tetrahedral?

Since PPh₃ is strong field ligand and, the famous Wilkinson's catalyst, which also possess this ligand is square planar, then what makes the above complex tetrahedral?
8
votes
1answer
1k views

What are the byproducts in a Suzuki reaction?

I am looking precisely at a coupling of a trifluoroborate with an aryl bromide. I know the mechanism of the Suzuki reaction, yet I cannot find any mention of the side products or degradation products ...
6
votes
1answer
71 views

Selective transfer of least/most stable anion from organometallic reagents

When heterocuprate reagents participate in conjugate addition, the least stable anion is transferred from copper to the electrophile: On the other hand, palladium-catalysed cross-coupling reactions ...
5
votes
1answer
101 views

How do the electronic properties of a catalyst affect the rate of oxidative addition?

In my project I have a coupling that was planned to be done using Pd (Suzuki or Stille possibly). Initially, I used an aryl chloride (the SM had already the chloride so I went with it), but the ...
4
votes
0answers
97 views

Ene-yne metathesis product

In the ene-yne metathesis how to know which product will form predominately, as the mechanisms to both are plausible?
1
vote
1answer
117 views

How does the bite angle of a ligand affect the efficiency of its catalyst?

I know that optimising the bite angle of a diphosphine ligand to its metal increases catalytic efficiency, and for cross-coupling reactions larger bite angles are favoured, but how does this have an ...