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1.
J Org Chem ; 88(16): 11702-11711, 2023 Aug 18.
Artigo em Inglês | MEDLINE | ID: mdl-37427877

RESUMO

Iridium(III)-catalyzed C-H cyclization of sulfoximines with diazo Meldrum's acid provided cyclic sulfoximines with a carbonyl group in good to excellent yields. These compounds were easily converted into unsubstituted and arylated sulfoximines. Moreover, the vinyl triflates obtained from the cyclic sulfoximines underwent palladium(II)-catalyzed cross-coupling reactions with a variety of aryl, arylalkynyl, and heteroatom (N and S) nucleophiles, affording a wide range of monosubstituted sulfoximines in high yields.

2.
J Org Chem ; 86(21): 15153-15163, 2021 Nov 05.
Artigo em Inglês | MEDLINE | ID: mdl-34592103

RESUMO

A direct B(4)-H monoacyloxylation via a Pd-catalyzed regioselective B(4)-H activation of o-carborane acids with phenyliodonium dicarboxylates was developed, and a series of B(4)-H monoacyloxylated o-carboranes decorated with active groups were synthesized with moderate to good yields as well as excellent selectivity. In addition, a direct B(4,5)-H diacetoxylation from o-carborane acids with phenyliodonium diacetate was demonstrated.

3.
Org Lett ; 26(39): 8410-8415, 2024 Oct 04.
Artigo em Inglês | MEDLINE | ID: mdl-39320152

RESUMO

Rh(III)-catalyzed B(4)-azo coupling reactions of o-carborane acids with aryl diazonium tetrafluoroborates have been developed, leading to the regioselective formation of B(4)-azo-coupled o-carboranes. Moreover, B(4)-azo-coupled o-carboranes can be further functionalized by introducing a second azo group, producing B(4)-C(1)-di(arylazo) o-carborane. The B(4)-azo group as an efficient directing group enables catalytic C-H amidation reactions, providing a new synthetic route for complex o-carborane derivatives.

4.
Org Lett ; 25(36): 6643-6648, 2023 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-37646852

RESUMO

Iridium(I)-catalyzed regioselective B(4)-alkenylation has been developed from o-carboranyl sulfoxonium ylides and alkynes through B(4)-H activation. The sequential B(4)- and B(6)-alkenylation afforded B(3,5)-dialkenylated o-carboranyl sulfoxonium ylides in one pot. Eventually, two alkenyl groups, the same or different, were introduced at positions 3 and 5 of the carborane. Sulfoxonium ylide used as a directing group remains available for further functionalization and is converted to B-alkenylated o-carboranyl trichloromethyl ketones.

5.
Org Lett ; 25(32): 5989-5994, 2023 Aug 18.
Artigo em Inglês | MEDLINE | ID: mdl-37540091

RESUMO

Iridium(III)-catalyzed regioselective B(4)-H amination is developed from the reaction of o-carborane acids with sulfilimines without any oxidants under mild conditions, which leads to a wide range of B(4)-H aminated o-carboranes in good yields with a broad substrate scope. Moreover, the selective B(3,6)-diamination reaction of the o-carborane acid was achieved. The present reaction is attractive from a practical point of view because dibenzothiophene is quantitatively recovered and reused.

6.
Org Lett ; 24(8): 1604-1609, 2022 Mar 04.
Artigo em Inglês | MEDLINE | ID: mdl-35175779

RESUMO

An iridium(III)-catalyzed regioselective acylmethylation of the cage B(4)-H bond in o-carborane acids with sulfoxonium ylides is demonstrated through B(4)-H activation in ethanol under very mild conditions, affording a number of B(4)-acylmethylated o-carboranes. Additionally, the selective sequential B(4)- and B(6)-acylmethylation reactions finally gave B(3,5)-diacylmethylated o-carboranes in one pot.

7.
Chem Asian J ; 16(20): 3179-3187, 2021 Oct 18.
Artigo em Inglês | MEDLINE | ID: mdl-34387948

RESUMO

An efficient synthetic method for structurally various isochromenoindolones has been demonstrated through Rh(III)-catalyzed C-H activation followed by a cyclization reaction of N-methoxyarylamides with 3-diazooxindoles. The sequential reaction involves the streamlined formation of C-C and C-O bonds in one pot. The present method provides a broad range of isochromenoindolones as a new privileged scaffold in moderate to good yields with the release of methoxyamine and molecular nitrogen and has the benefits of a broad substrate scope and good functional group tolerance.

8.
Org Lett ; 22(18): 7267-7272, 2020 Sep 18.
Artigo em Inglês | MEDLINE | ID: mdl-32877601

RESUMO

Described herein is the iridium-catalyzed sequential C(2)-arylation reaction and intramolecular C-O bond formation from azulenecarboxylic acids and diaryliodonium salts, leading to the formation of 3-arylazulenofuranones. The sequential reaction proceeded smoothly through generation of 2-arylazulene-1-carboxylic acids derived from the iridium-catalyzed regioselective C(2)-arylation reaction without the decarboxylation reaction.

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