Is it possible for me to alkylate my compound with the present of dioxaborolane in my compound?
Most papers get their compounds alkylated first (as shown in the attachment).
What I intend to do is to get my step4 done first, followed by step3. This is because I ordered my alkyl chains late..>
Shu Er Tan:
The alkylation of NH unit followed by C-B coupling reaction is the appropriate synthetic strategy used for the preparation of borate esters/boronic acids. It produces high yield of borate etser/boronic acids, by avoiding side reactions. In contrast, a consecutive N-alkylation reaction after C-B coupling might be complicated, on a substrate mentioned in the attachment. Borate ester units are generally sensitive to the bases. The substrate can lead to polymerization, through a homo coupling reaction, mediated by cleavage of C-B bond. For a possible alternative, the K2CO3 in acetonitrile under inert atmosphere can be attempted.
Hi Shu,
I think you'd better to wait until your orders arrive. Changing the sequence of the reaction might likely end you up with complicated reaction mixtures.
Assoc Prof Ramin Zibaseresht
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