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Catalytic Chan – Lam coupling using a ‘ tube-in-tube ’ reactor to deliver molecular oxygen as an oxidant

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ABSTRACT

A flow system to perform Chan–Lam coupling reactions of various amines and arylboronic acids has been realised employing molecular oxygen as an oxidant for the re-oxidation of the copper catalyst enabling a catalytic process. A tube-in-tube gas reactor has been used to simplify the delivery of the oxygen accelerating the optimisation phase and allowing easy access to elevated pressures. A small exemplification library of heteroaromatic products has been prepared and the process has been shown to be robust over extended reaction times.

No MeSH data available.


General flow scheme for catalytic Chan–Lam reaction.
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Figure 1: General flow scheme for catalytic Chan–Lam reaction.

Mentions: The use of oxygen provides the necessary oxidant to reoxidise the Cu(I) that forms after the C–N reductive elimination back to Cu(II), allowing for sub-stoichiometric amounts of copper catalyst to be used [15–16]. Based upon our previous experience of using the reverse “tube-in-tube” reactor with other gases, it was decided that oxygen would be delivered via this reactor set-up (Fig. 1).


Catalytic Chan – Lam coupling using a ‘ tube-in-tube ’ reactor to deliver molecular oxygen as an oxidant
General flow scheme for catalytic Chan–Lam reaction.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC4979635&req=5

Figure 1: General flow scheme for catalytic Chan–Lam reaction.
Mentions: The use of oxygen provides the necessary oxidant to reoxidise the Cu(I) that forms after the C–N reductive elimination back to Cu(II), allowing for sub-stoichiometric amounts of copper catalyst to be used [15–16]. Based upon our previous experience of using the reverse “tube-in-tube” reactor with other gases, it was decided that oxygen would be delivered via this reactor set-up (Fig. 1).

View Article: PubMed Central - HTML - PubMed

ABSTRACT

A flow system to perform Chan–Lam coupling reactions of various amines and arylboronic acids has been realised employing molecular oxygen as an oxidant for the re-oxidation of the copper catalyst enabling a catalytic process. A tube-in-tube gas reactor has been used to simplify the delivery of the oxygen accelerating the optimisation phase and allowing easy access to elevated pressures. A small exemplification library of heteroaromatic products has been prepared and the process has been shown to be robust over extended reaction times.

No MeSH data available.