Copper-Mediated sp2 C–H Chlorination with Trichloroacetamide Using a Removable Directing Group

Wan-Chen Cindy Lee; Arya Tehrani; Jie Jack Li

doi:10.1055/s-0036-1590503

Synthesis, Inhaltsverzeichnis

Synthesis 2017; 49(13): 2865-2872
DOI: 10.1055/s-0036-1590503

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Copper-Mediated sp ² C–H Chlorination with Trichloroacetamide Using a Removable Directing Group

Wan-Chen Cindy Lee

Department of Chemistry, University of San Francisco, 2130 Fulton Street, San Francisco, CA 94117, USA eMail: jjli@usfca.edu

,

Arya Tehrani

Department of Chemistry, University of San Francisco, 2130 Fulton Street, San Francisco, CA 94117, USA eMail: jjli@usfca.edu

,

Jie Jack Li *

Department of Chemistry, University of San Francisco, 2130 Fulton Street, San Francisco, CA 94117, USA eMail: jjli@usfca.edu

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Abstract

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Dedicated to Prof. David R. Williams at Indiana University

Abstract

2-Aminophenyl-1H-pyrazole was discovered as a removable, bidentate directing group for copper-mediated aerobic oxidative sp ² C–H bond chlorination employing trichloroacetamide as a new chlorine source. When Cu(OAc)₂ was employed as the copper source, 1,1,3,3-tetramethylguanidine (TMG) as an organic base, the reaction, optimally carried out overnight in DMSO at 80 °C in open air, produced a variety of mono- and dichlorinated products in moderate to excellent yields. This directing group can be removed oxidatively with cerium ammonium nitrate (CAN).

Key words

C–H chlorination - copper-mediated - trichloroacetamide - removable directing group - 2-aminophenyl-1H-pyrazole

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Referenzen

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18 See reference 3 for cost calculation and comparison.

Zusatzmaterial

Supporting Information

Copper-Mediated sp 2 C–H Chlorination with Trichloroacetamide Using a Removable Directing Group

Copper-Mediated sp ² C–H Chlorination with Trichloroacetamide Using a Removable Directing Group