Browse
Submit Data
Databases
API
Help

Dataset Information

39 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Rhodium-catalyzed synthesis of 2,3-disubstituted indoles from β,β-disubstituted stryryl azides.

ABSTRACT:

SUBMITTER: Sun K

PROVIDER: S-EPMC3154515 | biostudies-literature | 2011 Feb

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Rhodium-catalyzed synthesis of 2,3-disubstituted indoles from β,β-disubstituted stryryl azides.

Sun Ke K Liu Sheng S Bec Patryk M PM Driver Tom G TG

Angewandte Chemie (International ed. in English) 20110114 7

PMID: 21308937

Similar Datasets

Palladium-catalyzed beta-allylation of 2,3-disubstituted indoles.

Project description:Given the prevalence of the indole nucleus in biologically active compounds, the direct C3-functionalization of 2,3-disubstituted indoles represents an important problem. Described is a general, high-yielding method for the palladium-catalyzed beta-allylation of carba- and heterocycle fused indoles, including complex natural product substrates.

| S-EPMC3380807 | biostudies-literature

Synthesis of 3,3'-Disubstituted Indolenines Utilizing the Lewis Acid Catalyzed Alkylation of 2,3-Disubstituted Indoles with Trichloroacetimidates.

Project description:Trichloroacetimidates function as effective electrophiles for the selective C3-alkylation of 2,3-disubstituted indoles to provide 3,3'-disubstituted indolenines. These indolenines are common synthetic intermediates that are often utilized in the synthesis of complex molecules. Effective reaction conditions utilizing Lewis acid catalysts have been determined, and the scope of the reaction with respect to indole and imidate reaction partner has been investigated. This chemistry provides an alternative to base promoted and transition metal catalyzed methods that are more commonly utilized to access similar indolenines.

| S-EPMC5636001 | biostudies-literature

Brønsted acid catalyzed remote C6 functionalization of 2,3-disubstituted indoles with β,γ-unsaturated α-ketoester

Project description:Graphical Abstract A metal-free catalytic approach for the remote C6-functionalization of 2,3-disubstituted indoles has been developed. In the presence of catalytic amounts of Brønsted acid, the β,γ-unsaturated α-ketoesters react with 2,3-disubstituted indoles at the C6 position selectively. Under mild reaction conditions, a range of C6-functionalized indoles were prepared with good yields and excellent regioselectivity. This methodology provides a concise and efficient route for the synthesis of C6-functionalized indole derivatives.

| S-EPMC9513241 | biostudies-literature

Fe(II)-catalyzed amination of aromatic C-H bonds via ring opening of 2H-azirines: synthesis of 2,3-disubstituted indoles.

Project description:A general method for the synthesis of 2,3-disubstituted indoles is described. The key feature of this method is the amination of aromatic C-H bonds via FeCl(2)-catalyzed ring opening of 2H-azirines. The method tolerates a variety of functional groups such as Br, F, NO(2), OMe, CF(3), OTBS, alkenes, and OPiv. The method can also be extended to synthesize azaindoles.

| S-EPMC2955291 | biostudies-literature

Highly diastereo- and enantioselective CuH-catalyzed synthesis of 2,3-disubstituted indolines.

Project description:A diastereo- and enantioselective CuH-catalyzed method for the preparation of highly functionalized indolines is reported. The mild reaction conditions and high degree of functional group compatibility as demonstrated with substrates bearing heterocycles, olefins, and substituted aromatic groups, renders this technique highly valuable for the synthesis of a variety of cis-2,3-disubstituted indolines in high yield and enantioeselectivity.

| S-EPMC4440622 | biostudies-literature

Rhodium(I)-Catalyzed Benzannulation of Heteroaryl Propargylic Esters: Synthesis of Indoles and Related Heterocycles.

Project description:A de novo synthesis of a benzene ring allows for the preparation of a diverse range of heterocycles including indoles, benzofurans, benzothiophenes, carbazoles, and dibenzofurans from simple heteroaryl propargylic esters using a unified carbonylative benzannulation strategy. Multiple substituents can be easily introduced to the C4-C7 positions of indoles and related heterocycles.

| S-EPMC4945426 | biostudies-literature

Rhodium(iii)-catalyzed C-H allylation of indoles with allyl alcohols via β-hydroxide elimination.

Project description:An efficient Rh(iii)-catalyzed dehydrative C-H allylation of indoles with allyl alcohols via β-hydroxide elimination under oxidant-free conditions has been developed. This method features very mild reaction conditions, excellent regioselectivity and stereoselectivity, and compatibility with various functional groups. In addition, the directing group can be removed under mild reaction conditions, which further underscores the synthetic utility of this method.

| S-EPMC6135611 | biostudies-literature

Rhodium-catalyzed, P-directed selective C7 arylation of indoles.

Project description:The indole scaffold will continue to play a vital role in the future of drug discovery and agrochemical development. Regioselective direct arylation of indoles on the benzenoid moiety is a challenging task due to the inherent reactivity of the C2 and C3 positions. Here, we have developed an effective strategy for the regioselective direct arylation of indoles at the C7 position with (hetero)aryl bromides by the rational design of a directing group. The key to the high selectivity and reactivity of this method is the appropriate selection of a class of directing groups, N-PR2 (R = t Bu and c Hex), that are easily removed in the presence of the Wilkinson's catalyst. Using the present method as a key step, formal synthesis of marine alkaloid dictyodendrin B has also been demonstrated.

| S-EPMC6294599 | biostudies-literature

Rhodium(II)-catalyzed enantioselective C-H functionalization of indoles.

Project description:A catalytic, enantioselective method for the C-H functionalization of indoles by diazo compounds has been achieved. With catalytic amounts of Rh(2)(S-NTTL)(4), the putative Rh-carbene intermediates from α-alkyl-α-diazoesters react with indoles at C(3) to provide α-alkyl-α-indolylacetates in high yield and enantioselectivity. From DFT calculations, a mechanism is proposed that involves a Rh-ylide intermediate with oxocarbenium character.

| S-EPMC3144986 | biostudies-literature

Rhodium- and platinum-catalyzed [4+3] cycloaddition with concomitant indole annulation: synthesis of cyclohepta[b]indoles.

Project description: Not available

| S-EPMC3690624 | biostudies-literature