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An efficient method of accessing new CF3-containing spiro-[indene-proline] derivatives has been developed based on a Cp*Rh(III)-catalyzed tandem C-H activation/[3+2]–annulation reaction of 5-aryl-2-(trifluoromethyl)-3,4-dihydro-2H-pyrrole-2-carboxylates with alkynes. An important feature of this spiro annulation process is the feasibility of dehydroproline moiety to act as a directing group in the selective activation of the aromatic C-H bond. [ABSTRACT FROM AUTHOR]

A convenient pathway to a new series of α-CF3-substituted α-amino acid derivatives bearing pharmacophore isoquinolone core in their backbone has been developed. The method is based on [4+2]-annulation of N-(pivaloyloxy) aryl amides with orthogonally protected internal acetylene-containing α-amino carboxylates under Rh(III)-catalysis. The target annulation products can be easily transformed into valuable isoquinoline derivatives via a successive aromatization/cross-coupling operation. [ABSTRACT FROM AUTHOR]

An efficient pathway to a new family of fluorinated polyheteroaromatic D‐A molecules has been developed. The method is based on the Rh(III)‐catalyzed regioselective [4+2]‐annulation of N‐(pivaloyloxy)‐benzamides with 4‐ethynyl‐5,6‐difluoro‐7‐(p‐methoxyphenyl)‐2,1,3‐benzothiadiazole as a key step followed by the aromatization/Suzuki coupling sequence to furnish the target D‐A systems with modifiable acceptor block. The discovered difference in reactivity between ArB(OH)2 and ArBPin allows performing a divergent modification of BTD acceptor block by the manipulation of aryl boronic reagents in the ortho‐selective C−F activation of the fluorinated BTD moiety under Suzuki reaction conditions to furnish new D1‐π‐A‐D2 systems in good yields. Such step‐by‐step modification of the acceptor block has been achieved by Pd‐catalyzed C−F bond activation under isoquinoline ring assistance for the first time. [ABSTRACT FROM AUTHOR]

An efficient strategy for the preparation of a novel series of benzothiadiazole‐containing isoquinoline‐bridged D‐A compounds based on Cp*Rh(III)‐catalyzed redox‐neutral annulation of N‐(pivaloyloxy)‐benzamides with 4‐ethynyl‐7‐(p‐methoxyphenyl)‐2,1,3‐benzothiadiazole as a key step followed by the installation of donor units, such as diphenylamine, carbazole, and dihydrodibenzoazepine, by aromatization and Suzuki coupling reactions, has been developed. An initial photophysical, electrochemical and DFT investigations of the selected products have been performed. [ABSTRACT FROM AUTHOR]

A series of new orthogonally protected α‐CF3‐substituted α‐amino carboxylates, and α‐amino phosphonates decorated with pharmacophore isoquinolone core has been elaborated through the Rh(III)‐catalyzed C−H activation/annulation of aryl hydroxamates with propargyl‐containing α‐amino acid derivatives and their phosphorus analogues. [ABSTRACT FROM AUTHOR]