I'm trying to synthesize an aryl-alkyl bonding compound using suzuki-miyaura coupling reaction or whatelse.
Normaly, when we try to do it, we use aryl-X and alkyl-Bpin.
So, I would like to ask if it is possible to use aryl-Bpin and alkyl-X.
Or if who knows the better ways, pls let me know.
(I want to use aryl-X or aryl-Bpin and alkyl-X)
aryl-BPin and alkyl-X will still work but you might have harder time.
Oxidative addition into alkyl-X is more difficult than aryl-X. The same is true for reductive elimination. Also alkyl-X are prone to side reactions once oxidative addition occurs.
i am also appriciate to Greg answer but you still try varyout some solvent, ligand and longer reaction time. i suggest one paper download and please read it
Hanh Nho Nguyen, Xiaohua Huang, and Stephen L. Buchwald J. AM. CHEM. SOC. 2003, 125, 11818-11819
Yes it is possible to use aryl-Bpin and alkyl-X. Please see this paper.
Enantiospecific Synthesis of ortho-Substituted 1,1-Diarylalkanes by a 1,2-Metalate Rearrangement/anti-SN2’ Elimination/Rearomatizing Allylic Suzuki–Miyaura Reaction Sequence
Bel8n Rubial+ , Beatrice S. L. Collins+ , Raphael Bigler, Stefan Aichhorn, Adam Noble, and Varinder K. Aggarwal*
DOI: 10.1002/ange.201811343
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