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Rapid Coupling of Methyl Iodide with Aryltributylstannanes Mediated by Palladium(0) Complexes: A General Protocol for the Synthesis of 11 CH 3 ‐Labeled PET Tracers
Author(s) -
Suzuki Masaaki,
Doi Hisashi,
Björkman Margareta,
Andersson Yvonne,
Långström Bengt,
Watanabe Yasuyoshi,
Noyori Ryoji
Publication year - 1997
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19970031219
Subject(s) - iodide , methyl iodide , chemistry , yield (engineering) , tin , salt (chemistry) , palladium , ligand (biochemistry) , realization (probability) , medicinal chemistry , radiochemistry , inorganic chemistry , organic chemistry , catalysis , materials science , receptor , statistics , mathematics , metallurgy , biochemistry
Abstract The reaction of methyl iodide and (excess) aryltributylstannane to give a methylarene has been studied with the focus on the realization of rapid coupling for incorporation of short‐lived radionuclides into bioactive organic compounds. The coupling of methyl iodide with tributylphenylstannane (40 equiv) is accomplished in >90% yield within 5 min at 60°C with a tri‐ o ‐tolylphosphine‐bound, coordinatively unsaturated Pd 0 complex together with a Cu I salt and K 2 CO 3 in DMF. This protocol is applicable to a variety of homo‐ and heteroaromatic tin compounds, to give the corresponding methylated derivatives. The effects of the tri‐ o ‐tolylphosphine ligand, a Cu(I) salt, and DMF are discussed. This new protocol provides a firm chemical basis for the synthesis of 11 CH 3 ‐incorporated PET tracers.