Communication
Palladium-Catalyzed Decarbonylative Difluoromethylation of Acid Chlorides at Room Temperature
Dr. Fei Pan,
Dr. Gregory B. Boursalian,
Prof. Dr. Tobias Ritter,
Dr. Fei Pan
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
Search for more papers by this authorDr. Gregory B. Boursalian
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Tobias Ritter
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
Search for more papers by this authorDr. Fei Pan,
Dr. Gregory B. Boursalian,
Prof. Dr. Tobias Ritter,
Dr. Fei Pan
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
Search for more papers by this authorDr. Gregory B. Boursalian
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Tobias Ritter
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
Search for more papers by this authorGraphical Abstract
A palladium-catalyzed decarbonylative cross-coupling reaction of acid chlorides with a difluoromethyl zinc reagent allows access to difluoromethylated compounds. The transformation proceeds at room temperature and shows broad functional group tolerance, thus providing a general and efficient method for decarbonylative difluoromethylation of a wide range of aromatic carboxylic acids.
Abstract
Methods for the direct synthesis of difluoromethylated arenes are sparse, despite the importance of the difluoromethyl group in medical, agro-, and materials chemistry. A palladium-catalyzed decarbonylative cross-coupling reaction of acid chlorides with a difluoromethyl zinc reagent is achieved to access difluoromethylated compounds. The transformation proceeds at room temperature and shows broad functional group tolerance, thus providing a general and efficient method for decarbonylative difluoromethylation of a wide range of aromatic carboxylic acids.
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References
- 1
- 1aR. D. Chambers, Fluorine in Organic Chemistry, Blackwell publishing, Oxford, 2004;
10.1002/9781444305371 Google Scholar
- 1bK. Müller, C. Faeh, F. Diederich, Science 2007, 317, 1881–1886;
- 1cS. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320–330;
- 1dD. O'Hagan, Chem. Soc. Rev. 2008, 37, 308–319;
- 1eJ. Wang, M. Sánchez-Roselló, J. L. Aceňa, C. del Pozo, A. E. Sorochinsky, S. Fustero, V. A. Soloshonok, H. Liu, Chem. Rev. 2014, 114, 2432–2506;
- 1fQ.-H. Liu, C.-F. Ni, J.-B. Hu, Natl. Sci. Rev. 2017, 4, 303–325.
- 2
- 2aS. Swallow, Prog. Med. Chem. 2015, 54, 65–133;
- 2bE. P. Gillis, K. J. Eastman, M. D. Hill, D. J. Donnelly, N. A. Meanwell, J. Med. Chem. 2015, 58, 8315–8359;
- 2cY. Zhou, J. Wang, Z.-N. Gu, S.-N. Wang, W. Zhu, J. L. Aceña, V. A. Soloshonok, K. Izawa, H. Liu, Chem. Rev. 2016, 116, 422–518.
- 3
- 3aJ. A. Erickson, J. I. McLoughlin, J. Org. Chem. 1995, 60, 1626–1631;
- 3bM. A. Chowdhury, K. R. A. Abdellatif, Y. Dong, D. Das, M. R. Suresh, E. E. Knaus, J. Med. Chem. 2009, 52, 1525–1529;
- 3cC. D. Sessler, M. Rahm, S. Becker, J. M. Goldberg, F. Wang, S. L. Lippard, J. Am. Chem. Soc. 2017, 139, 9325–9332.
- 4For recent reviews, see:
- 4aP. Xu, S. Guo, L.-Y. Wang, P.-P. Tang, Synlett 2014, 26, 36–39;
- 4bB. Chen, D. A. Vicic, Top. Organomet. Chem. 2015, 52, 113–142;
- 4cM. C. Belhomme, T. Besset, T. Poisson, X. Pannecoucke, Chem. Eur. J. 2015, 21, 12836–12865;
- 4dJ. Rong, C.-F. Ni, J.-B. Hu, Asian J. Org. Chem. 2017, 6, 139–152;
- 4eD. E. Yerien, S. Barata-Vallejo, A. Postigo, Chem. Eur. J. 2017, 23, 14676–14701.
- 5For selected examples, see:
- 5aX.-L. Jiang, Z.-H. Chen, X.-H. Xu, F.-L. Qing, Org. Chem. Front. 2014, 1, 774–776;
- 5bC. Matheis, K. Jouvin, L. J. Goossen, Org. Lett. 2014, 16, 5984–5987;
- 5cJ. R. Bour, S. K. Kariofillis, M. S. Sanford, Organometallics 2017, 36, 1220–1223;
- 5dZ. Feng, Q.-Q. Min, X.-G. Zhang, Org. Lett. 2016, 18, 44–47;
- 5eX.-Y. Deng, J.-H. Lin, J.-C. Xiao, Org. Lett. 2016, 18, 4384–4387;
- 5fK. Aikawa, H. Serizawa, K. Ishii, K. Mikami, Org. Lett. 2016, 18, 3690–3693;
- 5gH. Serizawa, K. Ishii, K. Aikawa, K. Mikami, Org. Lett. 2016, 18, 3686–3689;
- 5hJ. Sheng, H.-Q. Ni, K.-J. Bian, Y. Li, Y.-N. Wang, X.-S. Wang, Org. Chem. Front. 2018, 5, 606–610.
- 6
- 6aY. Fujiwara, J. A. Dixon, R. A. Rodriguez, R. D. Baxter, D. D. Dixon, M. R. Collins, D. G. Blackmond, P. S. Baran, J. Am. Chem. Soc. 2012, 134, 1494–1497;
- 6bY. Fujiwara, J. A. Dixon, F. O'Hara, E. D. Funder, D. D. Dixon, R. A. Rodriguez, R. D. Baxter, B. Herlé, N. Sach, M. R. Collins, Y. Ishihara, P. S. Baran, Nature 2012, 492, 95–99;
- 6cS. Mizuta, I. S. R. Stenhagen, M. O'Duill, J. Wolstenhulme, A. K. Kirjavainen, S. J. Forsback, M. Tredwell, G. Sandford, P. R. Moore, M. Huiban, S. K. Luthra, J. Passchier, O. Solin, V. Gouverneur, Org. Lett. 2013, 15, 2648–2651;
- 6dJ.-B. Xia, C. Zhu, C. Chen, J. Am. Chem. Soc. 2013, 135, 17494–17500;
- 6eP. Xu, S. Guo, L. Wang, P.-P. Tang, Angew. Chem. Int. Ed. 2014, 53, 5955–5958; Angew. Chem. 2014, 126, 6065–6068.
- 7
- 7aD. R. Dodds, R. A. Gross, Science 2007, 318, 1250–1251;
- 7bR. A. Sheldon, Green Chem. 2014, 16, 950–963.
- 8
- 8aP. S. Fier, J. F. Hartwig, J. Am. Chem. Soc. 2012, 134, 5524–5527;
- 8bG. K. S. Prakash, S. K. Ganesh, J.-P. Jones, A. Kulkarni, K. Masood, J. K. Swabeck, G. A. Olah, Angew. Chem. Int. Ed. 2012, 51, 12090–12094; Angew. Chem. 2012, 124, 12256–12260.
- 9
- 9aY. Gu, X.-B. Leng, Q.-L. Shen, Nat. Commun. 2014, 5, 5405;
- 9bY. Gu, D.-L. Chang, X.-B. Leng, Y.-C. Gu, Q.-L. Shen, Organometallics 2015, 34, 3065–3071;
- 9cD.-L. Chang, Y. Gu, Q.-L. Shen, Chem. Eur. J. 2015, 21, 6074–6078.
- 10L. Xu, D. A. Vicic, J. Am. Chem. Soc. 2016, 138, 2536–2539.
- 11V. Bacauanu, S. Cardinal, M. Yamauchi, M. Kondo, D. F. Fernández, R. Remy, D. W. C. MacMillan, Angew. Chem. Int. Ed. 2018, 57, 12543–12548; Angew. Chem. 2018, 130, 12723–12728.
- 12Z. Feng, Q.-Q. Min, X.-P. Fu, L. An, X.-G. Zhang, Nat. Chem. 2017, 9, 918–923.
- 13W.-J. Miao, Y.-C. Zhao, C.-F. Ni, B. Gao, W. Zhang, J.-B. Hu, J. Am. Chem. Soc. 2018, 140, 880–883.
- 14For selected reviews, see:
- 14aL. J. Goossen, N. Rodríguez, K. Goossen, Angew. Chem. Int. Ed. 2008, 47, 3100–3120; Angew. Chem. 2008, 120, 3144–3164;
- 14bW. I. Dzik, P. P. Lange, L. J. Goossen, Chem. Sci. 2012, 3, 2671–2678;
- 14cR. Takise, K. Muto, J. Yamaguchi, Chem. Soc. Rev. 2017, 46, 5864–5888;
- 14dT. Patra, D. Maiti, Chem. Eur. J. 2017, 23, 7382–7401;
- 14eL. Guo, M. Rueping, Chem. Eur. J. 2018, 24, 7794–7809;
- 14fL. Guo, M. Rueping, Acc. Chem. Res. 2018, 51, 1185–1195.
- 15For selected examples, see:
- 15aB. M. Trost, F. Chen, Tetrahedron Lett. 1971, 12, 2603–2607;
10.1016/S0040-4039(01)96930-8 Google Scholar
- 15bE. M. O'Brien, E. A. Bercot, T. Rovis, J. Am. Chem. Soc. 2003, 125, 10498–10499;
- 15cX. Zhao, Z.-K. Yu, J. Am. Chem. Soc. 2008, 130, 8136–8137;
- 15dA. Correa, J. Cornella, R. Martin, Angew. Chem. Int. Ed. 2013, 52, 1878–1880; Angew. Chem. 2013, 125, 1928–1930;
- 15eA. Maleckis, M. S. Sanford, Organometallics 2014, 33, 2653–2660;
- 15fJ.-F. Hu, Y. Zhao, J.-J. Liu, Y.-M. Zhang, Z.-Z. Shi, Angew. Chem. Int. Ed. 2016, 55, 8718–8722; Angew. Chem. 2016, 128, 8860–8864;
- 15gC. A. Malapit, N. Ichiishi, M. S. Sanford, Org. Lett. 2017, 19, 4142–4145;
- 15hR. Takise, R. Isshiki, K. Muto, K. Itami, J. Yamaguchi, J. Am. Chem. Soc. 2017, 139, 3340–3343;
- 15iH. Ochiai, Y. Uetake, T. Niwa, T. Hosoya, Angew. Chem. Int. Ed. 2017, 56, 2482–2486; Angew. Chem. 2017, 129, 2522–2526;
- 15jT. Okita, K. Kumazawa, R. Takise, K. Muto, K. Itami, J. Yamaguchi, Chem. Lett. 2017, 46, 218–220;
- 15kA. Dey, S. Sasmal, K. Seth, G. K. Lahiri, D. Maiti, ACS Catal. 2017, 7, 433–437;
- 15lX.-Q. Liu, J.-Q. Jia, M. Rueping, ACS Catal. 2017, 7, 4491–4496;
- 15mG.-R. Meng, M. Szostak, ACS Catal. 2017, 7, 7251–7256;
- 15nA. Chatupheeraphat, H. Liao, S. Lee, M. Rueping, Org. Lett. 2017, 19, 4255–4258;
- 15oM. De La Higuera Macias, B. A. Arndtsen, J. Am. Chem. Soc. 2018, 140, 10140–10144;
- 15pA. Chatupheeraphat, H. Liao, W. Srimontree, L. Guo, Y. Minenkov, A. Poater, L. Cavallo, M. Rueping, J. Am. Chem. Soc. 2018, 140, 3724–3735;
- 15qN. Ichiishi, C. A. Malapit, L. Woźniak, M. S. Sanford, Org. Lett. 2018, 20, 44–47.
- 16For selected examples about decarbonylative Heck reactions, see:
- 16aH. Blaser, A. Spencer, J. Organomet. Chem. 1982, 233, 267–274;
- 16bM. S. Stephan, A. J. J. M. Teunissen, G. K. M. Verzijl, J. G. de Vries, Angew. Chem. Int. Ed. 1998, 37, 662–664;
10.1002/(SICI)1521-3773(19980316)37:5<662::AID-ANIE662>3.0.CO;2-0 CAS PubMed Web of Science® Google ScholarAngew. Chem. 1998, 110, 688–690;
- 16cL. J. Goossen, J. Paetzold, Angew. Chem. Int. Ed. 2002, 41, 1237–1241;
10.1002/1521-3773(20020402)41:7<1237::AID-ANIE1237>3.0.CO;2-F CAS PubMed Web of Science® Google ScholarAngew. Chem. 2002, 114, 1285–1289;
- 16dT. Sugihara, T. Satoh, M. Miura, M. Nomura, Angew. Chem. Int. Ed. 2003, 42, 4672–4674; Angew. Chem. 2003, 115, 4820–4822;
- 16eG.-R. Meng, M. Szostak, Angew. Chem. Int. Ed. 2015, 54, 14518–14522; Angew. Chem. 2015, 127, 14726–14730;
- 16fC.-W. Liu, G.-R. Meng, M. Szostak, J. Org. Chem. 2016, 81, 12023–12030.
- 17For selected examples about decarbonylative Suzuki reactions, see:
- 17aL. J. Goossen, J. Paetzold, Adv. Synth. Catal. 2004, 346, 1665–1668;
- 17bK. Muto, J. Yamaguchi, D. G. Musaev, K. Itami, Nat. Commun. 2015, 6, 7508;
- 17cN. A. Weires, E. L. Baker, N. K. Garg, Nat. Chem. 2016, 8, 75–79;
- 17dS.-C. Shi, G.-R. Meng, M. Szostak, Angew. Chem. Int. Ed. 2016, 55, 6959–6963; Angew. Chem. 2016, 128, 7073–7077;
- 17eJ. Masson-Makdissi, J. K. Vandavasi, S. G. Newman, Org. Lett. 2018, 20, 4094–4098.
- 18For selected examples about decarbonylative addition reactions, see:
- 18aY. Kajita, T. Kurahashi, S. Matsubara, J. Am. Chem. Soc. 2008, 130, 17226–17227;
- 18bY. Ochi, T. Kurahashi, S. Matsubara, Org. Lett. 2011, 13, 1374–1377;
- 18cE. N. Jenkins, W. L. Czaplyski, E. J. Alexanian, Org. Lett. 2017, 19, 2350–2353.
- 19S. T. Keaveney, F. Schoenebeck, Angew. Chem. Int. Ed. 2018, 57, 4073–4077; Angew. Chem. 2018, 130, 4137–4141.
- 20For selected examples about transition-metal-mediated decarbonylation process at room temperature, see:
- 20aJ. Tsuji, K. Ohno, Tetrahedron Lett. 1965, 6, 3969–3971;
- 20bK. Ohno, J. Tsuji, J. Am. Chem. Soc. 1968, 90, 99–107;
- 20cG. R. Clark, W. R. Roper, L. J. Wright, V. P. D. Yap, Organometallics 1997, 16, 5135–5136;
- 20dR. Ciganda, M. A. Garralda, L. Ibarlucea, C. Mendicute-Fierro, M. C. Torralba, M. R. Tprres, Inorg. Chem. 2012, 51, 1760–1768.
- 21K. Aikawa, Y. Nakamura, Y. Yokota, W. Toya, K. Mikami, Chem. Eur. J. 2015, 21, 96–100.
- 22A. J. Borah, G.-B. Yan, Org. Biomol. Chem. 2015, 13, 8094–8115.
- 23Y. Obora, Y. Tsuji, T. Kawamura, J. Am. Chem. Soc. 1993, 115, 10414–10415.
- 24
- 24aJ. S. Quesnel, B. A. Arndtsen, J. Am. Chem. Soc. 2013, 135, 16841–16844;
- 24bJ. S. Quesnel, L. V. Kayser, A. Fabrikant, B. A. Arndtsen, Chem. Eur. J. 2015, 21, 9550–9555.
- 25
- 25aR. Martin, S. L. Buchwald, Acc. Chem. Res. 2008, 41, 1461–1473;
- 25bT. Iwai, T. Fujihara, J. Terao, Y. Tsuji, J. Am. Chem. Soc. 2009, 131, 6668–6669.
- 26K. Tatsumi, R. Hoffmann, A. Yamamoto, J. K. Stille, Bull. Chem. Soc. Jpn. 1981, 54, 1857–1867.
- 27For selected reviews, see:
- 27aJ. K. Stille, Angew. Chem. Int. Ed. Engl. 1986, 25, 508–524; Angew. Chem. 1986, 98, 504–519;
- 27bM. Blangetti, H. Rosso, C. Prandi, A. Deagostino, P. Venturello, Molecules 2013, 18, 1188–1213; For selected examples, see:
- 27cD. Milstein, J. K. Stille, J. Am. Chem. Soc. 1978, 100, 3636–3638;
- 27dD. Milstein, J. K. Stille, J. Org. Chem. 1979, 44, 1613–1618;
- 27eA. M. Forbes, G. P. Meier, E. Jones-Mensah, J. Magolan, Eur. J. Org. Chem. 2016, 2983–2987.
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