Iridium(III)-Catalyzed CH Amidation of Arylphosphoryls Leading to a P-Stereogenic Center
Direct CH amidation of arylphosphoryl compounds has been developed by using an IrIII catalyst system under mild conditions. A wide range of substrates could be employed with high functional‐group tolerance. This procedure was successfully applied for the first time to the asymmetric reaction giving...
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| Published in | Chemistry : a European journal Vol. 20; no. 39; pp. 12421 - 12425 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
22.09.2014
WILEY‐VCH Verlag Wiley |
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| Abstract | Direct CH amidation of arylphosphoryl compounds has been developed by using an IrIII catalyst system under mild conditions. A wide range of substrates could be employed with high functional‐group tolerance. This procedure was successfully applied for the first time to the asymmetric reaction giving rise to a P‐chirogenic center with a high diastereomeric ratio of up to 19:1 (90 % de).
A road to P‐chirality: A cationic [IrIII(Cp*)] complex catalyzes the direct CH amidation of diarylphosphorus compounds bearing a chiral auxiliary to allow for a straightforward route to optically pure P‐chiral compounds (see scheme; Cp*=1,2,3,4,5‐pentamethylcyclopentadiene). |
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| AbstractList | Direct CH amidation of arylphosphoryl compounds has been developed by using an Ir(III) catalyst system under mild conditions. A wide range of substrates could be employed with high functional-group tolerance. This procedure was successfully applied for the first time to the asymmetric reaction giving rise to a P-chirogenic center with a high diastereomeric ratio of up to 19:1 (90 % de). Direct C-H amidation of arylphosphoryl compounds has been developed by using an Ir super(III) catalyst system under mild conditions. A wide range of substrates could be employed with high functional-group tolerance. This procedure was successfully applied for the first time to the asymmetric reaction giving rise to a P-chirogenic center with a high diastereomeric ratio of up to 19:1 (90%de). A road to- P-chirality: A cationic [Ir super(III)(Cp*)] complex catalyzes the direct C-H amidation of diarylphosphorus compounds bearing a chiral auxiliary to allow for a straightforward route to optically pure P-chiral compounds (see scheme; Cp*=1,2,3,4,5-pentamethylcyclopentadiene). Abstract Direct CH amidation of arylphosphoryl compounds has been developed by using an Ir III catalyst system under mild conditions. A wide range of substrates could be employed with high functional‐group tolerance. This procedure was successfully applied for the first time to the asymmetric reaction giving rise to a P‐chirogenic center with a high diastereomeric ratio of up to 19:1 (90 % de ). Direct C-H amidation of arylphosphoryl compounds has been developed by using an Ir-III catalyst system under mild conditions. A wide range of substrates could be employed with high functional-group tolerance. This procedure was successfully applied for the first time to the asymmetric reaction giving rise to a P-chirogenic center with a high diastereomeric ratio of up to 19:1 (90% de). Direct CH amidation of arylphosphoryl compounds has been developed by using an IrIII catalyst system under mild conditions. A wide range of substrates could be employed with high functional‐group tolerance. This procedure was successfully applied for the first time to the asymmetric reaction giving rise to a P‐chirogenic center with a high diastereomeric ratio of up to 19:1 (90 % de). A road to P‐chirality: A cationic [IrIII(Cp*)] complex catalyzes the direct CH amidation of diarylphosphorus compounds bearing a chiral auxiliary to allow for a straightforward route to optically pure P‐chiral compounds (see scheme; Cp*=1,2,3,4,5‐pentamethylcyclopentadiene). |
| Author | Park, Sehoon Gwon, Donghyeon Chang, Sukbok Kim, Jiyu Lee, Donggun |
| Author_xml | – sequence: 1 givenname: Donghyeon surname: Gwon fullname: Gwon, Donghyeon organization: Center for Catalytic Hydrocarbon Functionalizations, Institute of Basic Science (IBS), Daejeon 305-701 (Republic of Korea) – sequence: 2 givenname: Donggun surname: Lee fullname: Lee, Donggun organization: Center for Catalytic Hydrocarbon Functionalizations, Institute of Basic Science (IBS), Daejeon 305-701 (Republic of Korea) – sequence: 3 givenname: Jiyu surname: Kim fullname: Kim, Jiyu organization: Center for Catalytic Hydrocarbon Functionalizations, Institute of Basic Science (IBS), Daejeon 305-701 (Republic of Korea) – sequence: 4 givenname: Sehoon surname: Park fullname: Park, Sehoon email: sehoonp@kaist.ac.kr organization: Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701 (Republic of Korea) – sequence: 5 givenname: Sukbok surname: Chang fullname: Chang, Sukbok email: sbchang@kaist.ac.kr organization: Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701 (Republic of Korea) |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/25145858$$D View this record in MEDLINE/PubMed |
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| Keywords | asymmetric induction ASYMMETRIC-SYNTHESIS CARBON AZIDES chirality ARYLATION COMPLEXES ARENES iridium catalysis C-H functionalization phosphine oxides LIGANDS BOND ACTIVATION CH functionalization |
| Language | English |
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| Snippet | Direct CH amidation of arylphosphoryl compounds has been developed by using an IrIII catalyst system under mild conditions. A wide range of substrates could... Direct C-H amidation of arylphosphoryl compounds has been developed by using an Ir-III catalyst system under mild conditions. A wide range of substrates could... Direct CH amidation of arylphosphoryl compounds has been developed by using an Ir(III) catalyst system under mild conditions. A wide range of substrates could... Abstract Direct CH amidation of arylphosphoryl compounds has been developed by using an Ir III catalyst system under mild conditions. A wide range of... Direct C-H amidation of arylphosphoryl compounds has been developed by using an Ir super(III) catalyst system under mild conditions. A wide range of substrates... |
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| SubjectTerms | asymmetric induction Asymmetry Bearing Catalysts Cationic Chemistry Chemistry, Multidisciplinary chirality CH functionalization iridium catalysis phosphine oxides Physical Sciences Roads Science & Technology Tolerances |
| Title | Iridium(III)-Catalyzed CH Amidation of Arylphosphoryls Leading to a P-Stereogenic Center |
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