Regiodivergent cascade cyclization/alkoxylation of allenamides N-protecting group driven rearrangement to access indole and indoline derivatives

Regiodivergent cascade cyclization/alkoxylation of allenamides N-protecting group driven rearrangement to access indole and indoline derivatives

A mild, palladium-catalyzed domino Heck-cyclization/alkoxylation sequence of aryl halide tethered allenamides is described, providing regiodivergent indole and indoline derivatives controlled by the N-protecting group. This room temperature reaction provided a functionalizable olefinic moiety with b...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2022-10, Vol.58 (8), p.113-1133
Hauptverfasser: Chaudhary, Dhananjay, Yadav, Suman, Maurya, Naveen Kumar, Kumar, Dharmendra, Ishu, Km, Kuram, Malleswara Rao
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container_end_page 1133
container_issue 8
container_start_page 113
container_title Chemical communications (Cambridge, England)
container_volume 58
creator Chaudhary, Dhananjay
Yadav, Suman
Maurya, Naveen Kumar
Kumar, Dharmendra
Ishu, Km
Kuram, Malleswara Rao
description A mild, palladium-catalyzed domino Heck-cyclization/alkoxylation sequence of aryl halide tethered allenamides is described, providing regiodivergent indole and indoline derivatives controlled by the N-protecting group. This room temperature reaction provided a functionalizable olefinic moiety with broad substrate scope. Preliminary mechanistic studies support the rearrangement of an indoline-derived intermediate to indoles with the N -acetyl allenamides forming free (NH) indoles. A mild, palladium-catalyzed domino Heck-cyclization/alkoxylation sequence of aryl halide tethered allenamides was developed, providing regiodivergent indole and indoline derivatives controlled by the N-protecting group.
doi_str_mv 10.1039/d2cc03174d
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title Regiodivergent cascade cyclization/alkoxylation of allenamides N-protecting group driven rearrangement to access indole and indoline derivatives
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