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Redox‐Neutral Rhodium‐Catalyzed CH Functionalization of Arylamine N‐Oxides with Diazo Compounds: Primary C(sp3)H/C(sp2)H Activation and Oxygen‐Atom Transfer

An unprecedented rhodium(III)‐catalyzed regioselective redox‐neutral annulation reaction of 1‐naphthylamine N‐oxides with diazo compounds was developed to afford various biologically important 1‐benzo[g]indolines. This coupling reaction proceeds under mild reaction conditions and does not require ex... Full description

Journal Title: Angewandte Chemie International Edition 05 October 2015, Vol.54(41), pp.12121-12126
Main Author: Zhou, Bing
Other Authors: Chen, Zhaoqiang , Yang, Yaxi , Ai, Wen , Tang, Huanyu , Wu, Yunxiang , Zhu, Weiliang , Li, Yuanchao
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 1433-7851 ; E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201505302
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title: Redox‐Neutral Rhodium‐Catalyzed CH Functionalization of Arylamine N‐Oxides with Diazo Compounds: Primary C(sp3)H/C(sp2)H Activation and Oxygen‐Atom Transfer
format: Article
creator:
  • Zhou, Bing
  • Chen, Zhaoqiang
  • Yang, Yaxi
  • Ai, Wen
  • Tang, Huanyu
  • Wu, Yunxiang
  • Zhu, Weiliang
  • Li, Yuanchao
subjects:
  • Ch Activation
  • Density Functional Calculations
  • Heterocycles
  • Nitrogen Oxides
  • Rhodium
ispartof: Angewandte Chemie International Edition, 05 October 2015, Vol.54(41), pp.12121-12126
description: An unprecedented rhodium(III)‐catalyzed regioselective redox‐neutral annulation reaction of 1‐naphthylamine N‐oxides with diazo compounds was developed to afford various biologically important 1‐benzo[g]indolines. This coupling reaction proceeds under mild reaction conditions and does not require external oxidants. The only by‐products are dinitrogen and water. More significantly, this reaction represents the first example of dual functiaonalization of unactivated a primary C(sp)H bond and C(sp)H bond with diazocarbonyl compounds. DFT calculations revealed that an intermediate iminium is most likely involved in the catalytic cycle. Moreover, a rhodium(III)‐catalyzed coupling of readily available tertiary aniline N‐oxides with α‐diazomalonates was also developed under external oxidant‐free conditions to access various aminomandelic acid derivatives by an O‐atom‐transfer reaction. : The title reaction affords 1‐benzo[]indolines under mild reaction conditions and external oxidants are not required. The only by‐products are dinitrogen and water. This reaction represents the first example of dual functionalization of unactivated primary C(sp)H and C(sp)H bonds with diazocarbonyl compounds. Moreover, a method to access various aminomandelic acid derivatives by an O‐atom‐transfer strategy is described.
language: eng
source:
identifier: ISSN: 1433-7851 ; E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201505302
fulltext: fulltext
issn:
  • 1433-7851
  • 14337851
  • 1521-3773
  • 15213773
url: Link


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titleRedox‐Neutral Rhodium‐Catalyzed CH Functionalization of Arylamine N‐Oxides with Diazo Compounds: Primary C(sp3)H/C(sp2)H Activation and Oxygen‐Atom Transfer
creatorZhou, Bing ; Chen, Zhaoqiang ; Yang, Yaxi ; Ai, Wen ; Tang, Huanyu ; Wu, Yunxiang ; Zhu, Weiliang ; Li, Yuanchao
ispartofAngewandte Chemie International Edition, 05 October 2015, Vol.54(41), pp.12121-12126
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subjectCh Activation ; Density Functional Calculations ; Heterocycles ; Nitrogen Oxides ; Rhodium
descriptionAn unprecedented rhodium(III)‐catalyzed regioselective redox‐neutral annulation reaction of 1‐naphthylamine N‐oxides with diazo compounds was developed to afford various biologically important 1‐benzo[g]indolines. This coupling reaction proceeds under mild reaction conditions and does not require external oxidants. The only by‐products are dinitrogen and water. More significantly, this reaction represents the first example of dual functiaonalization of unactivated a primary C(sp)H bond and C(sp)H bond with diazocarbonyl compounds. DFT calculations revealed that an intermediate iminium is most likely involved in the catalytic cycle. Moreover, a rhodium(III)‐catalyzed coupling of readily available tertiary aniline N‐oxides with α‐diazomalonates was also developed under external oxidant‐free conditions to access various aminomandelic acid derivatives by an O‐atom‐transfer reaction. : The title reaction affords 1‐benzo[]indolines under mild reaction conditions and external oxidants are not required. The only by‐products are dinitrogen and water. This reaction represents the first example of dual functionalization of unactivated primary C(sp)H and C(sp)H bonds with diazocarbonyl compounds. Moreover, a method to access various aminomandelic acid derivatives by an O‐atom‐transfer strategy is described.
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titleRedox‐Neutral Rhodium‐Catalyzed CH Functionalization of Arylamine N‐Oxides with Diazo Compounds: Primary C(sp3)H/C(sp2)H Activation and Oxygen‐Atom Transfer
descriptionAn unprecedented rhodium(III)‐catalyzed regioselective redox‐neutral annulation reaction of 1‐naphthylamine N‐oxides with diazo compounds was developed to afford various biologically important 1‐benzo[g]indolines. This coupling reaction proceeds under mild reaction conditions and does not require external oxidants. The only by‐products are dinitrogen and water. More significantly, this reaction represents the first example of dual functiaonalization of unactivated a primary C(sp)H bond and C(sp)H bond with diazocarbonyl compounds. DFT calculations revealed that an intermediate iminium is most likely involved in the catalytic cycle. Moreover, a rhodium(III)‐catalyzed coupling of readily available tertiary aniline N‐oxides with α‐diazomalonates was also developed under external oxidant‐free conditions to access various aminomandelic acid derivatives by an O‐atom‐transfer reaction. : The title reaction affords 1‐benzo[]indolines under mild reaction conditions and external oxidants are not required. The only by‐products are dinitrogen and water. This reaction represents the first example of dual functionalization of unactivated primary C(sp)H and C(sp)H bonds with diazocarbonyl compounds. Moreover, a method to access various aminomandelic acid derivatives by an O‐atom‐transfer strategy is described.
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titleRedox‐Neutral Rhodium‐Catalyzed CH Functionalization of Arylamine N‐Oxides with Diazo Compounds: Primary C(sp3)H/C(sp2)H Activation and Oxygen‐Atom Transfer
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abstractAn unprecedented rhodium(III)‐catalyzed regioselective redox‐neutral annulation reaction of 1‐naphthylamine N‐oxides with diazo compounds was developed to afford various biologically important 1‐benzo[g]indolines. This coupling reaction proceeds under mild reaction conditions and does not require external oxidants. The only by‐products are dinitrogen and water. More significantly, this reaction represents the first example of dual functiaonalization of unactivated a primary C(sp)H bond and C(sp)H bond with diazocarbonyl compounds. DFT calculations revealed that an intermediate iminium is most likely involved in the catalytic cycle. Moreover, a rhodium(III)‐catalyzed coupling of readily available tertiary aniline N‐oxides with α‐diazomalonates was also developed under external oxidant‐free conditions to access various aminomandelic acid derivatives by an O‐atom‐transfer reaction. : The title reaction affords 1‐benzo[]indolines under mild reaction conditions and external oxidants are not required. The only by‐products are dinitrogen and water. This reaction represents the first example of dual functionalization of unactivated primary C(sp)H and C(sp)H bonds with diazocarbonyl compounds. Moreover, a method to access various aminomandelic acid derivatives by an O‐atom‐transfer strategy is described.
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pubWILEY‐VCH Verlag
doi10.1002/anie.201505302
pages12121-12126
date2015-10-05