Rhodium(iii)-catalyzed C-H activation at the C4-position of indole: Switchable hydroarylation and oxidative Heck-type reactions of maleimides

Mahadev Sharanappa Sherikar; Raja Kapanaiah; Veeranjaneyulu Lanke; Kandikere Ramaiah Prabhu

doi:10.1039/c8cc06264a

Rhodium(iii)-catalyzed C-H activation at the C4-position of indole: Switchable hydroarylation and oxidative Heck-type reactions of maleimides

Mahadev Sharanappa Sherikar
, Raja Kapanaiah
, Veeranjaneyulu Lanke
, Kandikere Ramaiah Prabhu

Research output: Contribution to journal › Article › peer-review

106 Scopus citations

Abstract

A Rh(iii)-catalyzed C-H activation of indole at the C4-position leading to novel and switchable functionalization has been reported by employing a weakly co-ordinating COCF₃ group as a directing group. An additive plays an important role in switching the selectivity between 1,4-addition products and Heck-type products. An acid additive led to the formation of 1,4-addition products whereas a base additive promotes the formation of Heck-type products. Deuteration studies and control experiments were helpful to propose the mechanism.

Original language	English
Pages (from-to)	11200-11203
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	79
DOIs	https://doi.org/10.1039/c8cc06264a
State	Published - 1 Jan 2018
Externally published	Yes

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "Rhodium(iii)-catalyzed C-H activation at the C4-position of indole: Switchable hydroarylation and oxidative Heck-type reactions of maleimides",

abstract = "A Rh(iii)-catalyzed C-H activation of indole at the C4-position leading to novel and switchable functionalization has been reported by employing a weakly co-ordinating COCF3 group as a directing group. An additive plays an important role in switching the selectivity between 1,4-addition products and Heck-type products. An acid additive led to the formation of 1,4-addition products whereas a base additive promotes the formation of Heck-type products. Deuteration studies and control experiments were helpful to propose the mechanism.",

author = "Sherikar, \{Mahadev Sharanappa\} and Raja Kapanaiah and Veeranjaneyulu Lanke and Prabhu, \{Kandikere Ramaiah\}",

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T1 - Rhodium(iii)-catalyzed C-H activation at the C4-position of indole

T2 - Switchable hydroarylation and oxidative Heck-type reactions of maleimides

AU - Sherikar, Mahadev Sharanappa

AU - Kapanaiah, Raja

AU - Lanke, Veeranjaneyulu

AU - Prabhu, Kandikere Ramaiah

PY - 2018/1/1

Y1 - 2018/1/1

N2 - A Rh(iii)-catalyzed C-H activation of indole at the C4-position leading to novel and switchable functionalization has been reported by employing a weakly co-ordinating COCF3 group as a directing group. An additive plays an important role in switching the selectivity between 1,4-addition products and Heck-type products. An acid additive led to the formation of 1,4-addition products whereas a base additive promotes the formation of Heck-type products. Deuteration studies and control experiments were helpful to propose the mechanism.

AB - A Rh(iii)-catalyzed C-H activation of indole at the C4-position leading to novel and switchable functionalization has been reported by employing a weakly co-ordinating COCF3 group as a directing group. An additive plays an important role in switching the selectivity between 1,4-addition products and Heck-type products. An acid additive led to the formation of 1,4-addition products whereas a base additive promotes the formation of Heck-type products. Deuteration studies and control experiments were helpful to propose the mechanism.

UR - https://www.scopus.com/pages/publications/85054093585

U2 - 10.1039/c8cc06264a

DO - 10.1039/c8cc06264a

M3 - Article

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JO - Chemical Communications

JF - Chemical Communications

IS - 79

ER -

Rhodium(iii)-catalyzed C-H activation at the C4-position of indole: Switchable hydroarylation and oxidative Heck-type reactions of maleimides

Abstract

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