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Beilstein J. Org. Chem. 2017, 13, 703–713, doi:10.3762/bjoc.13.69
Graphical Abstract
Scheme 1: Preparation of polyfluoroorganotrifluoroborates.
Scheme 2: Interaction of K[C6F5BF3] (1-K) with methyllithium (byproducts of hydrodeboration are not depicted)....
Scheme 3: Interaction of M[C6F5BF3] (1-M) with butyllithium (byproducts of hydrodeboration are not depicted).
Scheme 4: Interaction of K[C6F5BF3] (1-K) with phenyllithium (byproducts of hydrodeboration are not depicted)....
Scheme 5: Hydrodeboration of 6-K, 7-K, 8-K and 9-K in MeOH.
Scheme 6: Hydrodeboration of 1-K, 10-K and 11-K in methyl cellosolve.
Scheme 7: Hydrodeboration of 10-K, 11-K, 12-K and 13-K in MeOH.
Scheme 8: Preparation of 1-Li and 1-N.
Scheme 9: Formation of 2-R-tetrafluorophenyltrifluoroborates.
Scheme 10: Interaction between C6F5BF3− and PhLi.
Scheme 11: Interaction of 1-K with MeONa.
Scheme 12: Interaction of M[RC6F5BF3] with lithium halides.
Scheme 13: Assumed role of lithium halides.
Beilstein J. Org. Chem. 2015, 11, 608–616, doi:10.3762/bjoc.11.68
Scheme 1: The assumed silver(I) oxide assisted transmetallation with organoboronic acids.
Scheme 2: Cross-coupling of K[4-RC6F4BF3] (1a–r) with 3-IC6H4F (2) and 4-IC6H4F (3).
Scheme 3: Attempted synthesis of 7 (3’-F) and 8 (4’-F) by cross-coupling reaction.
Scheme 4: Synthesis of biphenyls 10a,c–f,h–p.
Scheme 5: Pd-catalyzed cross-coupling of 1a and salts 1b–p (1:1) with 11 (the results are presented in Table 3 and o...
Scheme 6: The cross-coupling of 1a with 11 in the presence of different silver(I) compounds.
Scheme 7: General concept of Pd-catalyzed Suzuki–Miyaura reaction.
Scheme 8: Assumed silver(I)-assisted transmetallation of weakly nucleophilic aryitrifluoroborates.