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Boraformylation and Silaformylation of Allenes
dc.contributor.authorFujihara, Tetsuaki
dc.contributor.authorSawada, Ayumi
dc.contributor.authorYamaguchi, Tatsuya
dc.contributor.authorTani, Yosuke
dc.contributor.authorTerao, Jun
dc.contributor.authorTsuji, Yasushi
dc.date.accessioned2017-06-16T20:16:16Z
dc.date.available2018-04-02T18:03:24Zen
dc.date.issued2017-02-01
dc.identifier.citationFujihara, Tetsuaki; Sawada, Ayumi; Yamaguchi, Tatsuya; Tani, Yosuke; Terao, Jun; Tsuji, Yasushi (2017). "Boraformylation and Silaformylation of Allenes." Angewandte Chemie International Edition 56(6): 1539-1543.
dc.identifier.issn1433-7851
dc.identifier.issn1521-3773
dc.identifier.urihttps://hdl.handle.net/2027.42/137579
dc.description.abstractThe boraformylation of allenes with B2(pin)2 and a formate ester as boron and formyl source, respectively, proceeds in the presence of a copper catalyst. The reaction selectively affords the corresponding β‐boryl β,γ‐unsaturated aldehydes in good to high yields. Furthermore, the silaformylation of allenes was achieved with a formate ester and PhMe2Si−B(pin) as the silicon source.Boron or silicon? Boraformylation and silaformylation reactions of allenes with formate esters smoothly proceed in the presence of a copper catalyst using B2(pin)2 and PhMe2Si−B(pin) as the boron and silicon source, respectively. These reactions selectively afford the corresponding β‐boryl and β‐silyl β,γ‐unsaturated aldehydes in good to high yields with excellent regioselectivity.
dc.publisherAldrich
dc.publisherWiley Periodicals, Inc.
dc.subject.othercopper
dc.subject.otherformate esters
dc.subject.othersilylation
dc.subject.otherborylation
dc.subject.otherallenes
dc.titleBoraformylation and Silaformylation of Allenes
dc.typeArticleen_US
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137579/1/anie201611314-sup-0001-misc_information.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137579/2/anie201611314_am.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137579/3/anie201611314.pdf
dc.identifier.doi10.1002/anie.201611314
dc.identifier.sourceAngewandte Chemie International Edition
dc.identifier.citedreferenceM. P. Doyle, M. S. Shanklin, Organometallics 1994, 13, 1081 – 1088;
dc.identifier.citedreference 
dc.identifier.citedreferenceI. Ojima, E. Vidal, M. Tzamarioudaki, I. Matsuda, J. Am. Chem. Soc. 1995, 117, 6797 – 6798;
dc.identifier.citedreferenceF. Monteil, I. Matsuda, H. Alper, J. Am. Chem. Soc. 1995, 117, 4419 – 4420; see also:
dc.identifier.citedreferenceI. Ojima, M. Tzamarioudaki, C. Y. Tsai, J. Am. Chem. Soc. 1994, 116, 3643 – 3644;
dc.identifier.citedreferenceI. Ojima, P. Ingallina, R. J. Donovan, N. Clos, Organometallics 1991, 10, 38 – 41;
dc.identifier.citedreferenceWhereas sodium propionate could also be used in the reaction, sodium laurate was preferred owing to its less hygroscopic nature.
dc.identifier.citedreferenceJ. L. Leighton, E. Chapman, J. Am. Chem. Soc. 1997, 119, 12416 – 12417.
dc.identifier.citedreferenceD. S. Laitar, P. Müller, J. P. Sadighi, J. Am. Chem. Soc. 2005, 127, 17196 – 17197.
dc.identifier.citedreferenceC. Kleeberg, M. S. Cheung, Z. Lin, T. B. Marder, J. Am. Chem. Soc. 2011, 133, 19060 – 190603.
dc.identifier.citedreferenceFor selected examples for β-borylallyl copper reagents generated from allenes and Cu−B species ( A b), see:
dc.identifier.citedreferenceK. Semba, N. Bessho, T. Fujihara, J. Terao, Y. Tsuji, Angew. Chem. Int. Ed. 2014, 53, 9007 – 9011; Angew. Chem. 2014, 126, 9153 – 9157;
dc.identifier.citedreferenceK. Semba, T. Fujihara, J. Terao, Y. Tsuji, Angew. Chem. Int. Ed. 2013, 52, 12400 – 12403; Angew. Chem. 2013, 125, 12626 – 12629;
dc.identifier.citedreferenceK. Semba, M. Shinomiya, T. Fujihara, J. Terao, Y. Tsuji, Chem. Eur. J. 2013, 19, 7125 – 7133;
dc.identifier.citedreferenceF. Meng, K. P. McGrath, A. H. Hoveyda, Nature 2014, 513, 367;
dc.identifier.citedreferenceF. Meng, H. Jang, B. Jung, A. H. Hoveyda, Angew. Chem. Int. Ed. 2013, 52, 5046 – 5051; Angew. Chem. 2013, 125, 5150 – 5155;
dc.identifier.citedreferenceW. Zhao, J. Montgomery, J. Am. Chem. Soc. 2016, 138, 9763 – 9766;
dc.identifier.citedreferenceJ. Rae, K. Yeung, J. J. McDouall, D. J. Procter, Angew. Chem. Int. Ed. 2016, 55, 1102 – 1107; Angew. Chem. 2016, 128, 1114 – 1119;
dc.identifier.citedreferenceK. Yeung, R. E. Ruscoe, J. Rae, A. P. Pulis, D. J. Procter, Angew. Chem. Int. Ed. 2016, 55, 11912 – 11916; Angew. Chem. 2016, 128, 12091 – 12095;
dc.identifier.citedreferenceY. Zhou, W. You, K. B. M. Smith, K. Brown, Angew. Chem. Int. Ed. 2014, 53, 3475 – 3479; Angew. Chem. 2014, 126, 3543 – 3547;
dc.identifier.citedreferenceW. Yuan, S. Ma, Adv. Synth. Catal. 2012, 354, 1867 – 1872.
dc.identifier.citedreferenceFor selected examples for β-silylallyl copper intermediates generated from allenes and Cu−Si species ( A si), see:
dc.identifier.citedreferenceY. Tani, T. Fujihara, J. Terao, Y. Tsuji, J. Am. Chem. Soc. 2014, 136, 2332 – 2333;
dc.identifier.citedreferenceY. Tani, Y. Yamaguchi, T. Fujihara, J. Terao, Y. Tsuji, Chem. Lett. 2015, 44, 271 – 273;
dc.identifier.citedreferenceZ.-T. He, X.-Q. Tang, L.-B. Xie, M. Cheng, P. Tian, G.-Q. Lin, Angew. Chem. Int. Ed. 2015, 54, 14815 – 14818; Angew. Chem. 2015, 127, 15028 – 15031;
dc.identifier.citedreferenceJ. Rae, Y. C. Hu, D. J. Procter, Chem. Eur. J. 2014, 20, 13143 – 13145;
dc.identifier.citedreferenceY.-H. Xu, L.-H. Wu, J. Wang, T.-P. Loh, Chem. Commun. 2014, 50, 7195 – 7197.
dc.identifier.citedreferenceFor the preparation of DTB-dppbz, see: T. Hatakeyama, T. Hashimoto, Y. Kondo, Y. Fujiwara, H. Seike, H. Takaya, Y. Tamada, T. Ono, M. Nakamura, J. Am. Chem. Soc. 2010, 132, 10674 – 10676.
dc.identifier.citedreference 
dc.identifier.citedreferenceN. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457 – 2483;
dc.identifier.citedreferenceA. Suzuki, H. C. Brown, Organic Syntheses via Boranes, Vol. 3, Aldrich, Milwaukee, 2003;
dc.identifier.citedreferenceT. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829 – 2844;
dc.identifier.citedreferenceN. Miyaura, Bull. Chem. Soc. Jpn. 2008, 81, 1535 – 1553;
dc.identifier.citedreferenceBoronic Acids, 2nd. ed. (Ed.: D. G. Hall ), Wiley-VCH, Weinheim, 2011;
dc.identifier.citedreferenceI. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 2010, 110, 890 – 931;
dc.identifier.citedreferenceE. C. Neeve, S. J. Geier, I. A. I. Mkhalid, S. A. Westcott, T. B. Marder, Chem. Rev. 2016, 116, 9091 – 9161.
dc.identifier.citedreferenceFor reviews on hydroboration, see:
dc.identifier.citedreferenceH. C. Brown, Pure Appl. Chem. 1976, 47, 49 – 60;
dc.identifier.citedreferenceL. Beletskaya, A. Pelter, Tetrahedron 1997, 53, 4957 – 5026;
dc.identifier.citedreferenceC. M. Crudden, D. Edwards, Eur. J. Org. Chem. 2003, 4695 – 4712;
dc.identifier.citedreferenceA.-M. Carroll, T. P. O’Sullivan, P. J. Guiry, Adv. Synth. Catal. 2005, 347, 609 – 631.
dc.identifier.citedreference 
dc.identifier.citedreferenceE. W. Colvin in Silicon in Organic Synthesis, Butterworths, London, 1981, pp.  44 – 82;
dc.identifier.citedreferenceE. W. Colvin in Silicon Reagents in Organic Synthesis, Academic, London, 1988, pp.  7 – 19;
dc.identifier.citedreferenceE. Langkopf, D. Schinzer, Chem. Rev. 1995, 95, 1375 – 1408;
dc.identifier.citedreferenceT. A. Blumenkopf, L. E. Overman, Chem. Rev. 1986, 86, 857 – 873;
dc.identifier.citedreferenceI. Fleming, J. Dunogues, R. Smithers, Org. React. 1989, 37, 57 – 575.
dc.identifier.citedreference 
dc.identifier.citedreferenceModern Allene Chemistry (Eds.: N. Krause, A. S. K. Hashmi ), Wiley-VCH, Weinheim, 2004;
dc.identifier.citedreferenceS. Ma, Chem. Rev. 2005, 105, 2829 – 2871;
dc.identifier.citedreferenceM. Jeganmohan, C.-H. Cheng, Chem. Commun. 2008, 3101 – 3117;
dc.identifier.citedreferenceS. Yu, S. Ma, Angew. Chem. Int. Ed. 2012, 51, 3074 – 3112; Angew. Chem. 2012, 124, 3128 – 3167.
dc.identifier.citedreferenceR. C. Larock, Comprehensive Organic Transformations, 2nd ed., Wiley-VCH, New York, 1999.
dc.identifier.citedreference 
dc.identifier.citedreferenceB. Breit, L. Diab in Comprehensive Organic Synthesis II, Vol. 4 (Eds.: P. Knochel, G. A. Molander ), Elsevier, Oxford, 2014, pp.  995 – 1053;
dc.identifier.citedreferenceI. Ojima, C. Y. Tsai, D. Tzamarioudaki, D. Bonafoux, Org. React. 2000, 56, 1 – 354.
dc.identifier.citedreference 
dc.identifier.citedreferenceR. P. Mariella, J. Am. Chem. Soc. 1947, 69, 2670 – 2672;
dc.identifier.citedreferenceR. L. Frank, R. H. Varland, Org. Synth. Coll. Vol. 1955, 3, 829 – 830.
dc.identifier.citedreferenceSee the Supporting Information for details.
dc.identifier.citedreferencedppe=1,2-bis(diphenylphosphino)ethane, xantphos=4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, dppbz=1,2-bis(diphenylphosphino)benzene, Xy-dppbz=1,2-bis(bis(3,5-dimethylphenyl)phosphino)benzene, DTB-dppbz=1,2-bis(bis(3,5-di- tert -butylphenyl)phosphino)benzene, DTBM-dppbz=1,2-bis(bis(3,5-di- tert -butyl-4-methoxyphenyl)phosphino)benzene, IPr=1,3-bis(2,6-diisopropylphenyl)imidazole-2-ylidene, IMes=1,3-bis(2,4,6-trimethylphenyl)imidazole-2-ylidene.
dc.identifier.citedreferenceL. Horner, H. Hoffmann, H. G. Wippel, Chem. Ber. 1958, 91, 61 – 63;
dc.identifier.citedreferenceW. S. Wadsworth,  Jr., W. D. Emmons, J. Am. Chem. Soc. 1961, 83, 1733 – 1738;
dc.identifier.citedreferenceS. K. Thompson, C. H. Heathcock, J. Org. Chem. 1990, 55, 3386 – 3388.
dc.identifier.citedreference 
dc.identifier.citedreferenceY. Katafuchi, T. Fujihara, T. Iwai, J. Terao, Y. Tsuji, Adv. Synth. Catal. 2011, 353, 475 – 482;
dc.identifier.citedreferenceT. Fujihara, T. Hosoki, Y. Katafuchi, T. Iwai, J. Terao, Y. Tsuji, Chem. Commun. 2012, 48, 8012 – 8014;
dc.identifier.citedreferenceT. Ueda, H. Konishi, K. Manabe, Org. Lett. 2012, 14, 3100 – 3103;
dc.identifier.citedreferenceY. Hoshimoto, T. Ohta, Y. Sasaoka, M. Ohashi, S. Ogoshi, J. Am. Chem. Soc. 2014, 136, 15877 – 15880;
dc.identifier.citedreferenceH. Li, H. Neumann, M. Beller, X.-F. Wu, Angew. Chem. Int. Ed. 2014, 53, 3183 – 3186; Angew. Chem. 2014, 126, 3247 – 3250.
dc.identifier.citedreference 
dc.identifier.citedreferenceI. Matsuda, A. Ogiso, S. Sato, Y. Izumi, J. Am. Chem. Soc. 1989, 111, 2332 – 2333;
dc.identifier.citedreferenceI. Matsuda, Y. Fukuta, T. Tsuchihashi, H. Nagashima, K. Itoh, Organometallics 1997, 16, 4327 – 4345;
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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