Carboxylation of Organoboronic Esters Catalyzed by N-Heterocyclic Carbene Copper(I) Complexes

Copper complexes with a CO2 fixation: Copper(I) complexes serve as excellent catalysts for the carboxylation of aryl‐ and alkenylboronic esters with CO2, affording a variety of functionalized carboxylic acid derivatives (see scheme). Important active intermediates such as the copper(I) aryl and carb...

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Published in	Angewandte Chemie International Edition Vol. 47; no. 31; pp. 5792 - 5795
Main Authors	Ohishi, Takeshi, Nishiura, Masayoshi, Hou, Zhaomin
Format	Journal Article
Language	English
Published	Weinheim Wiley-VCH Verlag 21.07.2008 WILEY-VCH Verlag WILEY‐VCH Verlag Wiley
Subjects	boronic esters carbene ligands carbon dioxide carboxylation Chemistry Chemistry, Multidisciplinary copper catalysts Physical Sciences Science & Technology carbon dioxide ALLYLIC CARBONATES carbene ligands EFFICIENT ROUTE DIOXIDE CO2 ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BORATION REDUCTION carboxylation HOMOGENEOUS CATALYSIS copper catalysts boronic esters METAL-COMPLEXES DIBORON
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Abstract	Copper complexes with a CO2 fixation: Copper(I) complexes serve as excellent catalysts for the carboxylation of aryl‐ and alkenylboronic esters with CO2, affording a variety of functionalized carboxylic acid derivatives (see scheme). Important active intermediates such as the copper(I) aryl and carboxylate complexes, [(IPr)CuR] and [(IPr)CuOCOR] (R=4‐MeOC6H4, IPr=1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene), are isolated and structurally characterized.
AbstractList	Copper complexes with a CO2 fixation: Copper(I) complexes serve as excellent catalysts for the carboxylation of aryl‐ and alkenylboronic esters with CO2, affording a variety of functionalized carboxylic acid derivatives (see scheme). Important active intermediates such as the copper(I) aryl and carboxylate complexes, [(IPr)CuR] and [(IPr)CuOCOR] (R=4‐MeOC6H4, IPr=1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene), are isolated and structurally characterized.
Author	Ohishi, Takeshi Nishiura, Masayoshi Hou, Zhaomin
Author_xml	– sequence: 1 fullname: Ohishi, Takeshi – sequence: 2 fullname: Nishiura, Masayoshi – sequence: 3 fullname: Hou, Zhaomin
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/18576463$$D View this record in MEDLINE/PubMed
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Keywords	carbon dioxide ALLYLIC CARBONATES carbene ligands EFFICIENT ROUTE DIOXIDE CO2 ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BORATION REDUCTION carboxylation HOMOGENEOUS CATALYSIS copper catalysts boronic esters METAL-COMPLEXES DIBORON
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Notes	http://dx.doi.org/10.1002/anie.200801857 ark:/67375/WNG-WHBQ3KCW-7 This work was partly supported by a Grant-in-aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan. We thank Mrs. Hu (RIKEN) for elemental analysis. ArticleID:ANIE200801857 istex:808A44D75405494F6B39FA50F8B06D4F3A70E4A7 Ministry of Education, Culture, Sports, Science and Technology of Japan This work was partly supported by a Grant‐in‐aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan. We thank Mrs. Hu (RIKEN) for elemental analysis. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
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References_xml	– reference: M. Takimoto, Y. Nakamura, K. Kimura, M. Mori, J. Am. Chem. Soc. 2004, 126, 5956-5957; – reference: H. Ito, C. Kawakami, M. Sawamura, J. Am. Chem. Soc. 2005, 127, 16034-16035; – reference: An analogous acetate complex [(IPr)CuOAc] was reported previously. See: T. G. David, D. S. Laiter, J. P. Sadighi, Organometallics 2004, 23, 1191-1193. – reference: N. P. Mankad, D. S. Laiter, J. P. Sadighi, Organometallics 2004, 23, 3369-3371. – reference: Purchased from Strem Chemicals, Inc. For preparation of IPr⋅HCl, see: A. J. Arduengo III, R. Krafczyk, R. Schmutzler, Tetrahedron 1999, 55, 14523-14534. – reference: H. Ito, H. Yamanaka, J. Tateiwa, A. Hosomi, Tetrahedron Lett. 2000, 41, 6821-6825; – reference: R. Wada, K. Oisaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 8910-8911; – reference: D. Walther, M. Ruben, S. Rau, Coord. Chem. Rev. 1999, 182, 67-100. – reference: V. Jurkauskas, J. P. Sadighi, S. L. Buchwald, Org. Lett. 2003, 5, 2417-2420; – reference: P. V. Ramachandran, D. Pratihar, D. Biswas, A. Srivastava, M. V. Ram. Reddy, Org. Lett. 2004, 6, 481-484; – reference: R. J. Franks, K. M. Nicholas, Organometallics 2000, 19, 1458-1460; – reference: S. Oi, Y. Fukue, K. Nemoto, Y. Inoue, Macromolecules 1996, 29, 2694-2695; – reference: H. Kaur, F. K. Zinn, E. D. Stevens, S. P. Nolan, Organometallics 2004, 23, 1157-1160. – reference: Angew. Chem. Int. Ed. Engl. 1988, 27, 661-678. – reference: S. Mun, J. E. Lee, J. Yun, Org. Lett. 2006, 8, 4887-4889; – reference: T. J. Marks, et al., Chem. Rev. 2001, 101, 953-996(see Supporting Information); – reference: T. Sakakura, J.-C. Choi, H. Yasuda, Chem. Rev. 2007, 107, 2365-2387; – reference: J. E. Lee, J. Kwon, Angew. Chem. 2008, 120, 151-153; – reference: Y. Fukue, S. Oi, Y. Inoue, J. Chem. Soc. Chem. Commun. 1994, 2091. – reference: Z. Hou, T. Ohishi in Comprehensive Organometallic Chemistry III, Vol. 10 (Eds.: R. H. Crabtree, D. M. P. Mingos, I. 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Snippet	Copper complexes with a CO2 fixation: Copper(I) complexes serve as excellent catalysts for the carboxylation of aryl‐ and alkenylboronic esters with CO2,...
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SubjectTerms	boronic esters carbene ligands carbon dioxide carboxylation Chemistry Chemistry, Multidisciplinary copper catalysts Physical Sciences Science & Technology
Title	Carboxylation of Organoboronic Esters Catalyzed by N-Heterocyclic Carbene Copper(I) Complexes
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