ChemInform Abstract: Unique Reactivity of Fluorinated Molecules with Transition Metals
Organofluorine and organometallic chemistry by themselves constitute two potent areas in organic synthesis. Thus, the combination of both offers many chemical possibilities and represents a powerful tool for the design and development of new synthetic methodologies leading to diverse molecular structures in an efficient manner. Given the importance of the selective introduction of fluorine atoms into organic molecules and the effectiveness of transition metals in C-C and C-heteroatom bond formation, this review represents an interesting read for this aim.
Direct Difluorination–Hydroxylation, Trifluorination, and C(sp2)–H Fluorination of Enamides
A direct double functionalization involving both difluorination and hydroxylation of enamides is reported. With the appropriate combination of an electrophilic fluorinating reagent and H2O, the most convenient and ecofriendly hydroxylating agent, the preparation of 3-(difluoroalkyl)-3-hydroxyisoindolin-1-ones was achieved under basic or Bronsted acidic conditions. Suitable conditions for trifluorination as well as C(sp2)–H fluorination were also identified. Subsequent asymmetric functionalization of the obtained gem-difluorinated products has also been demonstrated.
Synthesis of 3-substituted isoindolin-1-ones via a tandem desilylation, cross-coupling, hydroamidation sequence under aqueous phase-transfer conditions
A simple and expedient method for the synthesis of 3-methylene-isoindolin-1-ones 4 under aqueous phase-transfer conditions has been developed. Starting from 2-iodobenzamides 1 and (silyl) alkynes, the products are obtained in high yields and short reaction times (30 min) with the use of inexpensive CuCl/PPh3 catalyst system in the presence of n-Bu4NBr (TBAB) as a phase-transfer agent. Terminal alkynes are conveniently "unmasked" upon in situ desilylation under the reaction conditions. Alkynes possessing heterocyclic moieties were also found as amenable substrates. Furthermore, a one-pot process starting from 2-iodobenzamides 1, aryl halides (bromides or iodides) and trimethylsilylacetylene …
Unique Reactivity of Fluorinated Molecules with Transition Metals
Organofluorine and organometallic chemistry by themselves constitute two potent areas in organic synthesis. Thus, the combination of both offers many chemical possibilities and represents a powerful tool for the design and development of new synthetic methodologies leading to diverse molecular structures in an efficient manner. Given the importance of the selective introduction of fluorine atoms into organic molecules and the effectiveness of transition metals in C–C and C–heteroatom bond formation, this review represents an interesting read for this aim.
ChemInform Abstract: Synthesis of 3-Substituted Isoindolin-1-ones via a Tandem Desilylation, Cross-Coupling, Hydroamidation Sequence under Aqueous Phase-Transfer Conditions.
A simple and expedient method for the synthesis of 3-methylene-isoindolin-1-ones 4 under aqueous phase-transfer conditions has been developed. Starting from 2-iodobenzamides 1 and (silyl)alkynes, the products are obtained in high yields and short reaction times (30 min) with the use of inexpensive CuCl/PPh3 catalyst system in the presence of n-Bu4NBr (TBAB) as a phase-transfer agent. Terminal alkynes are conveniently “unmasked” upon in situ desilylation under the reaction conditions. Alkynes possessing heterocyclic moieties were also found as amenable substrates. Furthermore, a one-pot process starting from 2-iodobenzamides 1, aryl halides (bromides or iodides) and trimethylsilylacetylene (…
CCDC 1427402: Experimental Crystal Structure Determination
Related Article: Socrates B. Munoz, Alexandra N. Aloia, Alexander K. Moore, Attila Papp, Thomas Mathew, Santos Fustero, George A. Olah, G. K. Surya Prakash|2016|Org.Biomol.Chem.|14|85|doi:10.1039/C5OB02187A
CCDC 1426924: Experimental Crystal Structure Determination
Related Article: Socrates B. Munoz, Alexandra N. Aloia, Alexander K. Moore, Attila Papp, Thomas Mathew, Santos Fustero, George A. Olah, G. K. Surya Prakash|2016|Org.Biomol.Chem.|14|85|doi:10.1039/C5OB02187A