2019
DOI: 10.1021/acs.orglett.9b00150
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Directing-Group-Assisted Manganese-Catalyzed Cyclopropanation of Indoles

Abstract: The first manganese-catalyzed cyclopropanation of indoles is reported in moderate to excellent yield with methyl-2-diazo-2-arylacetates. This new strategy involved acetyl (COCH3) as the directing group and exhibited exceptional functional group tolerance. In the absence of stereodirecting groups the desired products were obtained as a mixture of diastereomers (7:3 → 8:2). Control experiments and DFT studies elucidated the probable pathway for the formation of cyclopropane-fused indole product. Deacetylation of… Show more

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Cited by 38 publications
(18 citation statements)
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“…Synthesis of aryl and 3‐thiophenyl diazo esters (2 a – i and k) : All aryl diazo acetates were prepared by reported procedure [10] . Aryl acetates (1 equiv., 5 mmol) were dissolved in acetonitrile (10 ml) in a clean oven dried round bottom flask, added DBU (1,8‐Diazabicyclo[5.4.0]undec‐7‐ene) (1.2 equiv., 6 mmol), stirred for 10 minutes, p‐ABSA (4‐Acetamidobenzenesulfonyl azide) (1.2 equiv., 6 mmol) was added, stirred for 4 hours in dark and r.t; after completion acetonitrile was removed under vacuum, diluted with ethyl acetate (25 ml), washed with water and organic layer was dried with brine and sodium sulphate, purified with flash column chromatography in silica gel (60–120 mesh size) with 5% ethyl acetate in hexane to yield 98% [10b] …”
Section: Methodsmentioning
confidence: 99%
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“…Synthesis of aryl and 3‐thiophenyl diazo esters (2 a – i and k) : All aryl diazo acetates were prepared by reported procedure [10] . Aryl acetates (1 equiv., 5 mmol) were dissolved in acetonitrile (10 ml) in a clean oven dried round bottom flask, added DBU (1,8‐Diazabicyclo[5.4.0]undec‐7‐ene) (1.2 equiv., 6 mmol), stirred for 10 minutes, p‐ABSA (4‐Acetamidobenzenesulfonyl azide) (1.2 equiv., 6 mmol) was added, stirred for 4 hours in dark and r.t; after completion acetonitrile was removed under vacuum, diluted with ethyl acetate (25 ml), washed with water and organic layer was dried with brine and sodium sulphate, purified with flash column chromatography in silica gel (60–120 mesh size) with 5% ethyl acetate in hexane to yield 98% [10b] …”
Section: Methodsmentioning
confidence: 99%
“…All aryl diazo acetates were prepared by reported procedure. [10] Aryl acetates (1 equiv., 5 mmol) were dissolved in acetonitrile (10 ml) in a clean oven dried round bottom flask, added DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene) (1.2 equiv., 6 mmol), Scheme 3. Probable reaction mechanism of C2À H activation of Pyrroles.…”
Section: Synthesis Of Aryl and 3-thiophenyl Diazo Esters (2 A-i And K)mentioning
confidence: 99%
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“…Based on our experimental observations and precedent literatures, [6,7,9b–d] we proposed the plausible catalytic cycle in Scheme 5. Initially, the Cp*Rh(OAc) 2 ‐mediated and the hydroxyl group‐directed C−H activation of 1 a proceeded to afford the rhodacycle A , followed by the regioselective alkyne insertion to give intermediate B .…”
Section: Methodsmentioning
confidence: 66%
“…Derivatives of 1H-indole-2-acetic acid are common, naturally occurring indoline alkaloids with important bioactivities [1][2][3][4][5][6][7][8][9][10]. These compounds were used as key intermediates in total syntheses of several natural products and nonnatural pharmaceutical agents [11][12][13][14][15][16][17]. Thus, synthetic methods for selective preparation of these 1H-indole derivatives remain the focus of many research groups.…”
Section: Introductionmentioning
confidence: 99%