Orthogonal Discrimination among Functional Groups in Ullmann-Type C–O and C–N Couplings
The copper-catalyzed arylation of nucleophiles has been established as an efficient methodology for the formation of C–C and C–heteroatom bonds. Considering the advances during the last two decades, the ligand choice plays a key role in such transformations and can strongly influence the catalytic e...
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| Published in | Journal of organic chemistry Vol. 81; no. 17; pp. 7315 - 7325 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
02.09.2016
Amer Chemical Soc |
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| Abstract | The copper-catalyzed arylation of nucleophiles has been established as an efficient methodology for the formation of C–C and C–heteroatom bonds. Considering the advances during the last two decades, the ligand choice plays a key role in such transformations and can strongly influence the catalytic efficiency. The applicability of these Ullmann-type coupling reactions regarding the orthogonal selectivity of different functional groups constitutes a challenging subject for current synthetic strategies. Herein, we report a useful toolkit of Cu-based catalysts for the chemoselective arylation of a wide-range of nucleophiles in competitive reactions using aryl iodides and bromides. We show in this work that the arylation of all kinds of amides can be orthogonal to that of amines (aliphatic or aromatic) and phenol derivatives. This high chemoselectivity can be governed by the use of different ligands, yielding the desired coupling products under mild conditions. The selectivity trends are maintained for electronically biased iodobenzene and bromobenzene electrophiles. Radical clock experiments discard the occurrence of radical-based mechanisms. |
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| AbstractList | The copper-catalyzed arylation of nucleophiles has been established as an efficient methodology for the formation of C–C and C–heteroatom bonds. Considering the advances during the last two decades, the ligand choice plays a key role in such transformations and can strongly influence the catalytic efficiency. The applicability of these Ullmann-type coupling reactions regarding the orthogonal selectivity of different functional groups constitutes a challenging subject for current synthetic strategies. Herein, we report a useful toolkit of Cu-based catalysts for the chemoselective arylation of a wide-range of nucleophiles in competitive reactions using aryl iodides and bromides. We show in this work that the arylation of all kinds of amides can be orthogonal to that of amines (aliphatic or aromatic) and phenol derivatives. This high chemoselectivity can be governed by the use of different ligands, yielding the desired coupling products under mild conditions. The selectivity trends are maintained for electronically biased iodobenzene and bromobenzene electrophiles. Radical clock experiments discard the occurrence of radical-based mechanisms. The copper-catalyzed arylation of nucleophiles has been established as an efficient methodology for the formation of C-C and C-heteroatom bonds. Considering the advances during the last two decades, the ligand choice plays a key role in such transformations and can strongly influence the catalytic efficiency. The applicability of these Ullmann-type coupling reactions regarding the orthogonal selectivity of different functional groups constitutes a challenging subject for current synthetic strategies. Herein, we report a useful toolkit of Cu-based catalysts for the chemoselective arylation of a wide-range of nucleophiles in competitive reactions using aryl iodides and bromides. We show in this work that the arylation of all kinds of amides can be orthogonal to that of amines (aliphatic or aromatic) and phenol derivatives. This high chemoselectivity can be governed by the use of different ligands, yielding the desired coupling products under mild conditions. The selectivity trends are maintained for electronically biased iodobenzene and bromobenzene electrophiles. Radical clock experiments discard the occurrence of radical-based mechanisms.The copper-catalyzed arylation of nucleophiles has been established as an efficient methodology for the formation of C-C and C-heteroatom bonds. Considering the advances during the last two decades, the ligand choice plays a key role in such transformations and can strongly influence the catalytic efficiency. The applicability of these Ullmann-type coupling reactions regarding the orthogonal selectivity of different functional groups constitutes a challenging subject for current synthetic strategies. Herein, we report a useful toolkit of Cu-based catalysts for the chemoselective arylation of a wide-range of nucleophiles in competitive reactions using aryl iodides and bromides. We show in this work that the arylation of all kinds of amides can be orthogonal to that of amines (aliphatic or aromatic) and phenol derivatives. This high chemoselectivity can be governed by the use of different ligands, yielding the desired coupling products under mild conditions. The selectivity trends are maintained for electronically biased iodobenzene and bromobenzene electrophiles. Radical clock experiments discard the occurrence of radical-based mechanisms. |
| Author | Soler, Marta Gómez, Laura Rovira, Mireia Güell, Imma Wang, Ming-Zheng Ribas, Xavi |
| AuthorAffiliation | Institut de Química Computacional i Catàlisi (IQCC) and Departament de Química Universitat de Girona, Campus de Montilivi Serveis Tècnics de Recerca (STR) Universitat de Girona, Parc Científic i Tecnològic de la UdG |
| AuthorAffiliation_xml | – name: Institut de Química Computacional i Catàlisi (IQCC) and Departament de Química – name: Universitat de Girona, Campus de Montilivi – name: Serveis Tècnics de Recerca (STR) – name: Universitat de Girona, Parc Científic i Tecnològic de la UdG |
| Author_xml | – sequence: 1 givenname: Mireia surname: Rovira fullname: Rovira, Mireia – sequence: 2 givenname: Marta surname: Soler fullname: Soler, Marta – sequence: 3 givenname: Imma surname: Güell fullname: Güell, Imma – sequence: 4 givenname: Ming-Zheng surname: Wang fullname: Wang, Ming-Zheng – sequence: 5 givenname: Laura surname: Gómez fullname: Gómez, Laura – sequence: 6 givenname: Xavi surname: Ribas fullname: Ribas, Xavi email: xavi.ribas@udg.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27249644$$D View this record in MEDLINE/PubMed |
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| Keywords | NITROGEN-CONTAINING HETEROCYCLES ROOM-TEMPERATURE MILD CONDITIONS CATALYZED CROSS-COUPLINGS ARYL HALIDES COPPER AMIDE BOND FORMATION VINYL HALIDES HIGHLY EFFICIENT ALKYL-HALIDES |
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| Snippet | The copper-catalyzed arylation of nucleophiles has been established as an efficient methodology for the formation of C–C and C–heteroatom bonds. Considering... The copper-catalyzed arylation of nucleophiles has been established as an efficient methodology for the formation of C-C and C-heteroatom bonds. Considering... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Orthogonal Discrimination among Functional Groups in Ullmann-Type C–O and C–N Couplings |
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