Diverse Approaches for Enantioselective C-H Functionalization Reactions Using Group 9 Cp

C−H activation asymmetric catalysis cobalt iridium rhodium

Journal

Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783

Informations de publication

Date de publication:
10 Jun 2020
Historique:
received: 30 11 2019
pubmed: 30 1 2020
medline: 30 1 2020
entrez: 30 1 2020
Statut: ppublish

Résumé

Transition-metal-catalyzed C-H functionalization reactions with Cp*M

Identifiants

pubmed: 31994236
doi: 10.1002/chem.201905417
doi:

Types de publication

Journal Article Review

Langues

eng

Sous-ensembles de citation

IM

Pagination

7346-7357

Subventions

Organisme : Japan Society for the Promotion of Science
ID : JP15H05802 in Precisely Designed Catalysts with Customized Scaffolding
Organisme : Japan Society for the Promotion of Science
ID : JP18H04637 in Hybrid Catalysis

Informations de copyright

© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Références

 
B. M. Trost, Science 1991, 254, 1471-1477;
P. A. Wender, B. L. Miller, Nature 2009, 460, 197-201;
N. Z. Burns, P. S. Baran, R. W. Hoffmann, Angew. Chem. Int. Ed. 2009, 48, 2854-2867;
Angew. Chem. 2009, 121, 2896-2910.
 
For selected recent general reviews on C−H functionalizations, see: Z. Dong, Z. Ren, S. J. Thompson, Y. Xu, G. Dong, Chem. Rev. 2017, 117, 9333-9403;
J. R. Hummel, J. A. Boerth, J. A. Ellman, Chem. Rev. 2017, 117, 9163-9227;
D. J. Abrams, P. A. Provencher, E. J. Sorensen, Chem. Soc. Rev. 2018, 47, 8925-8967;
R. R. Karimov, J. F. Hartwig, Angew. Chem. Int. Ed. 2018, 57, 4234-4241;
Angew. Chem. 2018, 130, 4309-4317;
C. Sambiagio, D. Schönbauer, R. Blieck, T. Dao-Huy, G. Pototschnig, P. Schaaf, T. Wiesinger, M. F. Zia, J. Wencel-Delord, T. Besset, B. U. W. Maes, M. Schnürch, Chem. Soc. Rev. 2018, 47, 6603-6743;
P. Gandeepan, T. Müller, D. Zell, G. Cera, S. Warratz, L. Ackermann, Chem. Rev. 2019, 119, 2192-2452.
 
T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212-11222;
N. Kuhl, N. Schröder, F. Glorius, Adv. Synth. Catal. 2014, 356, 1443-1460;
G. Song, X. Li, Acc. Chem. Res. 2015, 48, 1007-1020;
T. Yoshino, S. Matsunaga, Adv. Synth. Catal. 2017, 359, 1245-1262;
S. Wang, S.-Y. Chen, X.-Q. Yu, Chem. Commun. 2017, 53, 3165-3180;
P. G. Chirila, C. J. Whiteoak, Dalton Trans. 2017, 46, 9721-9739;
T. Piou, T. Rovis, Acc. Chem. Res. 2018, 51, 170-180;
J. Park, S. Chang, Chem. Asian J. 2018, 13, 1089-1102;
A. Peneau, C. Guillou, L. Chabaud, Eur. J. Org. Chem. 2018, 5777-5794.
 
K. Ueura, T. Satoh, M. Miura, Org. Lett. 2007, 9, 1407-1409;
K. Ueura, T. Satoh, M. Miura, J. Org. Chem. 2007, 72, 5362-5367.
 
T. Yoshino, H. Ikemoto, S. Matsunaga, M. Kanai, Angew. Chem. Int. Ed. 2013, 52, 2207-2211;
Angew. Chem. 2013, 125, 2263-2267;
B. Sun, T. Yoshino, S. Matsunaga, M. Kanai, Adv. Synth. Catal. 2014, 356, 1491-1495.
 
For reviews on enantioselective C−H activation/functionalization reactions, see: B. Ye, N. Cramer, Acc. Chem. Res. 2015, 48, 1308-1318;
C. G. Newton, D. Kossler, N. Cramer, J. Am. Chem. Soc. 2016, 138, 3935-3941;
C. G. Newton, S.-G. Wang, C. C. Oliveira, N. Cramer, Chem. Rev. 2017, 117, 8908-8976;
Y.-F. Yang, X. Hong, J.-Q. Yu, K. N. Houk, Acc. Chem. Res. 2017, 50, 2853-2860;
T. G. Saint-Denis, R.-Y. Zhu, G. Chen, Q.-F. Wu, J.-Q. Yu, Science 2018, 359, eaao4798;
J. Diesel, N. Cramer, ACS Catal. 2019, 9, 9164-9177;
G. Liao, T. Zhou, Q.-J. Yao, B.-F. Shi, Chem. Commun. 2019, 55, 8514-8523;
J. Loup, U. Dhawa, F. Pesciaioli, J. Wencel-Delord, L. Ackermann, Angew. Chem. Int. Ed. 2019, 58, 12803-12818;
Angew. Chem. 2019, 131, 12934-12949.
T. K. Hyster, L. Knörr, T. R. Ward, T. Rovis, Science 2012, 338, 500-503.
B. Ye, N. Cramer, Science 2012, 338, 504-506.
 
D. Lapointe, K. Fagnou, Chem. Lett. 2010, 39, 1118-1126;
L. Ackermann, Chem. Rev. 2011, 111, 1315-1345;
D. L. Davies, S. A. Macgregor, C. L. McMullin, Chem. Rev. 2017, 117, 8649-8709.
C−H activation processes similar to CMD are also called ambiphilic metal-ligand activation/assistance (AMLA) or base-assisted internal electrophilic substitution (BIES). Although the BIES mechanism is often discriminated from the others by the electronic effects of substrates on the reactivity, such a discrimination is not always obvious, as pointed out by Davies and Macgregor: R. A. Alharis, C. L. McMullin, D. L. Davies, K. Singh, S. A. Macgregor, J. Am. Chem. Soc. 2019, 141, 8896-8906.
They also suggested that CMD/AMLA/BIES can be essentially the same mechanism. Based on this, all related C−H activation processes are called ‘CMD’ in this Minireview. For the BIES mechanism, also see: J. Oxgaard, W. J. Tenn, R. J. Nielsen, R. A. Periana, W. A. Goddard, Organometallics 2007, 26, 1565-1567;
D. H. Ess, S. M. Bischof, J. Oxgaard, R. A. Periana, W. A. Goddard, Organometallics 2008, 27, 6440-6445;
W. Ma, R. Mei, G. Tenti, L. Ackermann, Chem. Eur. J. 2014, 20, 15248-15251.
 
Y. Park, S. Chang, Nat. Catal. 2019, 2, 219-227;
H. Wang, Y. Park, Z. Bai, S. Chang, G. He, G. Chen, J. Am. Chem. Soc. 2019, 141, 7194-7201.
 
For early examples of chiral Cpx ligands without additional coordination sites and their applications, see: R. L. Halterman, K. P. C. Vollhardt, Organometallics 1988, 7, 883-892;
G. Erker, A. A. H. van der Zeijden, Angew. Chem. Int. Ed. Engl. 1990, 29, 512-514;
Angew. Chem. 1990, 102, 543-545;
H. Schumann, O. Stenzel, S. Dechert, F. Girgsdies, J. Blum, D. Gelman, R. L. Halterman, Eur. J. Org. Chem. 2002, 211-219;
A. Gutnov, B. Heller, H.-J. Drexler, A. Spannenberg, G. Oehme, Organometallics 2003, 22, 1550-1553;
R. L. Halterman, L. D. Crow, Tetrahedron Lett. 2003, 44, 2907-2909;
A. Gutnov, H.-J. Drexler, A. Spannenberg, G. Oehme, B. Heller, Organometallics 2004, 23, 1002-1009;
A. Gutnov, B. Heller, C. Fischer, H.-J. Drexler, A. Spannenberg, B. Sundermann, C. Sundermann, Angew. Chem. Int. Ed. 2004, 43, 3795-3797;
Angew. Chem. 2004, 116, 3883-3886;
B. Heller, A. Gutnov, C. Fischer, H.-J. Drexler, A. Spannenberg, D. Redkin, C. Sundermann, B. Sundermann, Chem. Eur. J. 2007, 13, 1117-1128;
G. P. McGlacken, C. T. O'Brien, A. C. Whitwood, I. J. S. Fairlamb, Organometallics 2007, 26, 3722-3728;
M. Hapke, K. Kral, C. Fischer, A. Spannenberg, A. Gutnov, D. Redkin, B. Heller, J. Org. Chem. 2010, 75, 3993-4003.
Another report using Rh-1: C. Duchemin, N. Cramer, Chem. Sci. 2019, 10, 2773-2777.
B. Ye, N. Cramer, J. Am. Chem. Soc. 2013, 135, 636-639.
 
B. Ye, N. Cramer, Synlett 2015, 26, 1490-1495;
G. Smits, B. Audic, M. D. Wodrich, C. Corminboeuf, N. Cramer, Chem. Sci. 2017, 8, 7174-7179;
Y. Sun, N. Cramer, Chem. Sci. 2018, 9, 2981-2985;
C. Duchemin, G. Smits, N. Cramer, Organometallics 2019, 38, 3939-3947.
 
For examples, see: B. Ye, N. Cramer, Angew. Chem. Int. Ed. 2014, 53, 7896-7899;
Angew. Chem. 2014, 126, 8030-8033;
B. Ye, P. A. Donets, N. Cramer, Angew. Chem. Int. Ed. 2014, 53, 507-511;
Angew. Chem. 2014, 126, 517-521;
J. Zheng, S.-L. You, Angew. Chem. Int. Ed. 2014, 53, 13244-13247;
Angew. Chem. 2014, 126, 13460-13463;
S. Reddy Chidipudi, D. J. Burns, I. Khan, H. W. Lam, Angew. Chem. Int. Ed. 2015, 54, 13975-13979;
Angew. Chem. 2015, 127, 14181-14185;
M. V. Pham, N. Cramer, Chem. Eur. J. 2016, 22, 2270-2273;
T. J. Potter, D. N. Kamber, B. Q. Mercado, J. A. Ellman, ACS Catal. 2017, 7, 150-153;
X. Chen, S. Yang, H. Li, B. Wang, G. Song, ACS Catal. 2017, 7, 2392-2396;
X. Yang, G. Zheng, X. Li, Angew. Chem. Int. Ed. 2019, 58, 322-326;
Angew. Chem. 2019, 131, 328-332;
S.-G. Wang, N. Cramer, Angew. Chem. Int. Ed. 2019, 58, 2514-2518;
Angew. Chem. 2019, 131, 2536-2540;
R. Mi, G. Zheng, Z. Qi, X. Li, Angew. Chem. Int. Ed. 2019, 58, 17666-17670;
Angew. Chem. 2019, 131, 17830-17834;
S.-G. Wang, Y. Liu, N. Cramer, Angew. Chem. Int. Ed. 2019, 58, 18136-18140;
Angew. Chem. 2019, 131, 18304-18308.
B. Audic, M. D. Wodrich, N. Cramer, Chem. Sci. 2019, 10, 781-787.
J. Zheng, W.-J. Cui, C. Zheng, S.-L. You, J. Am. Chem. Soc. 2016, 138, 5242-5245.
 
For other applications of Rh-3, see: J. Zheng, S.-B. Wang, C. Zheng, S.-L. You, Angew. Chem. Int. Ed. 2017, 56, 4540-4544;
Angew. Chem. 2017, 129, 4611-4615;
T. Li, C. Zhou, X. Yan, J. Wang, Angew. Chem. Int. Ed. 2018, 57, 4048-4052;
Angew. Chem. 2018, 130, 4112-4116.
For related enantioselective synthesis of axially chiral products through C−H activation, see: H. Li, X. Yan, J. Zhang, W. Guo, J. Jiang, J. Wang, Angew. Chem. Int. Ed. 2019, 58, 6732-6736;
Angew. Chem. 2019, 131, 6804-6808. See also ref. 15c.
Z.-J. Jia, C. Merten, R. Gontla, C. G. Daniliuc, A. P. Antonchick, H. Waldmann, Angew. Chem. Int. Ed. 2017, 56, 2429-2434;
Angew. Chem. 2017, 129, 2469-2474.
 
M. Potowski, J. O. Bauer, C. Strohmann, A. P. Antonchick, H. Waldmann, Angew. Chem. Int. Ed. 2012, 51, 9512-9516;
Angew. Chem. 2012, 124, 9650-9654;
M. Potowski, A. P. Antonchick, H. Waldmann, Chem. Commun. 2013, 49, 7800-7802;
Z.-L. He, H.-L. Teng, C.-J. Wang, Angew. Chem. Int. Ed. 2013, 52, 2934-2938;
Angew. Chem. 2013, 125, 3006-3010.
 
For other applications of Rh-4, see: G. Shan, J. Flegel, H. Li, C. Merten, S. Ziegler, A. P. Antonchick, H. Waldmann, Angew. Chem. Int. Ed. 2018, 57, 14250-14254;
Angew. Chem. 2018, 130, 14446-14450;
H. Li, R. Gontla, J. Flegel, C. Merten, S. Ziegler, A. P. Antonchick, H. Waldmann, Angew. Chem. Int. Ed. 2019, 58, 307-311;
Angew. Chem. 2019, 131, 313-317.
S.-G. Wang, S. H. Park, N. Cramer, Angew. Chem. Int. Ed. 2018, 57, 5459-5462;
Angew. Chem. 2018, 130, 5557-5560.
 
H. Gotoh, R. Masui, H. Ogino, M. Shoji, Y. Hayashi, Angew. Chem. Int. Ed. 2006, 45, 6853-6856;
Angew. Chem. 2006, 118, 7007-7010;
H. Gotoh, H. Ogino, H. Ishikawa, Y. Hayashi, Tetrahedron 2010, 66, 4894-4899.
E. A. Trifonova, N. M. Ankudinov, A. A. Mikhaylov, D. A. Chusov, Y. V. Nelyubina, D. S. Perekalin, Angew. Chem. Int. Ed. 2018, 57, 7714-7718;
Angew. Chem. 2018, 130, 7840-7844.
D. Gwon, S. Park, S. Chang, Tetrahedron 2015, 71, 4504-4511.
Y. Sun, N. Cramer, Angew. Chem. Int. Ed. 2017, 56, 364-367;
Angew. Chem. 2017, 129, 370-373.
Y.-S. Jang, M. Dieckmann, N. Cramer, Angew. Chem. Int. Ed. 2017, 56, 15088-15092;
Angew. Chem. 2017, 129, 15284-15288.
 
Related cooperative catalysis of chiral CpxMIII and chiral carboxylic acid: Y.-S. Jang, L. Woźniak, J. Pedroni, N. Cramer, Angew. Chem. Int. Ed. 2018, 57, 12901-12905;
Angew. Chem. 2018, 130, 13083-13087;
Y. Sun, N. Cramer, Angew. Chem. Int. Ed. 2018, 57, 15539-15543;
Angew. Chem. 2018, 130, 15765-15769;
M. Brauns, N. Cramer, Angew. Chem. Int. Ed. 2019, 58, 8902-8906;
Angew. Chem. 2019, 131, 8994-8998.
Effects of achiral carboxylic acids on an enantioselective C−H activation: B. Shen, B. Wan, X. Li, Angew. Chem. Int. Ed. 2018, 57, 15534-15538;
Angew. Chem. 2018, 130, 15760-15764.
 
J. Zheng, S.-B. Wang, C. Zheng, S.-L. You, J. Am. Chem. Soc. 2015, 137, 4880-4883;
C. Zheng, J. Zheng, S.-L. You, ACS Catal. 2016, 6, 262-271. For related annulation reactions, see refs. 15d, 18a, and 22b.
M. Tian, D. Bai, G. Zheng, J. Chang, X. Li, J. Am. Chem. Soc. 2019, 141, 9527-9532.
S. Maity, T. J. Potter, J. A. Ellman, Nat. Catal. 2019, 2, 756-762.
K. Ozols, Y.-S. Jang, N. Cramer, J. Am. Chem. Soc. 2019, 141, 5675-5680.
I. S. Hassan, A. N. Ta, M. W. Danneman, N. Semakul, M. Burns, C. H. Basch, V. N. Dippon, B. R. McNaughton, T. Rovis, J. Am. Chem. Soc. 2019, 141, 4815-4819.
 
Chiral mono-protected amino acids (MPAA) and related ligands were successfully used in Pd-catalyzed enantioselective C−H activation/functionalization reactions. For pioneering work, see: B.-F. Shi, N. Maugel, Y.-H. Zhang, J.-Q. Yu, Angew. Chem. Int. Ed. 2008, 47, 4882-4886;
Angew. Chem. 2008, 120, 4960-4964.
Selected recent examples: G. Chen, W. Gong, Z. Zhuang, M. S. Andrä, Y.-Q. Chen, X. Hong, Y.-F. Yang, T. Liu, K. N. Houk, J.-Q. Yu, Science 2016, 353, 1023-1027;
Q. Shao, Q. F. Wu, J. He, J. Q. Yu, J. Am. Chem. Soc. 2018, 140, 5322-5325;
L. Hu, P.-X. Shen, Q. Shao, K. Hong, J. X. Qiao, J.-Q. Yu, Angew. Chem. Int. Ed. 2019, 58, 2134-2138;
Angew. Chem. 2019, 131, 2156-2160;
E. A. Romero, G. Chen, M. Gembicky, R. Jazzar, J.-Q. Yu, G. Bertrand, J. Am. Chem. Soc. 2019, 141, 16726-16733. See also refs. [6c-e].
L. Lin, S. Fukagawa, D. Sekine, E. Tomita, T. Yoshino, S. Matsunaga, Angew. Chem. Int. Ed. 2018, 57, 12048-12052;
Angew. Chem. 2018, 130, 12224-12228.
Y.-H. Liu, P.-X. Li, Q.-J. Yao, Z.-Z. Zhang, D.-Y. Huang, M. D. Le, H. Song, L. Liu, B. F. Shi, Org. Lett. 2019, 21, 1895-1899.
S. Fukagawa, Y. Kato, R. Tanaka, M. Kojima, T. Yoshino, S. Matsunaga, Angew. Chem. Int. Ed. 2019, 58, 1153-1157;
Angew. Chem. 2019, 131, 1165-1169.
For racemic reactions, see: P. W. Tan, A. M. Mak, M. B. Sullivan, D. J. Dixon, J. Seayad, Angew. Chem. Int. Ed. 2017, 56, 16550-16554;
Angew. Chem. 2017, 129, 16777-16781.
D. Sekine, K. Ikeda, S. Fukagawa, M. Kojima, T. Yoshino, S. Matsunaga, Organometallics 2019, 38, 3921-3926.
S. Fukagawa, M. Kojima, T. Yoshino, S. Matsunaga, Angew. Chem. Int. Ed. 2019, 58, 18154-18158;
Angew. Chem. 2019, 131, 18322-18326.
For racemic reactions, see: H. Wang, G. Tang, X. Li, Angew. Chem. Int. Ed. 2015, 54, 13049-13052;
Angew. Chem. 2015, 127, 13241-13244.
 
D. Zell, M. Bursch, V. Müller, S. Grimme, L. Ackermann, Angew. Chem. Int. Ed. 2017, 56, 10378-10382;
Angew. Chem. 2017, 129, 10514-10518;
F. Pesciaioli, U. Dhawa, J. C. A. Oliveira, R. Yin, M. John, L. Ackermann, Angew. Chem. Int. Ed. 2018, 57, 15425-15429;
Angew. Chem. 2018, 130, 15651-15655.
S. Satake, T. Kurihara, K. Nishikawa, T. Mochizuki, M. Hatano, K. Ishihara, T. Yoshino, S. Matsunaga, Nat. Catal. 2018, 1, 585-591.
 
For BINSA (1,1′-binaphthyl-2,2′-disulfonic acid) in asymmetric catalysis, see: M. Hatano, T. Maki, K. Moriyama, M. Arinobe, K. Ishihara, J. Am. Chem. Soc. 2008, 130, 16858-16860;
S. C. Pan, B. List, Chem. Asian J. 2008, 3, 430-437;
M. Hatano, K. Ishihara, Asian J. Org. Chem. 2014, 3, 352-365.
For SPISA (1,1′-spirobiindane-7,7′-disulfonic acid), see: T. Kurihara, S. Satake, M. Hatano, K. Ishihara, T. Yoshino, S. Matsunaga, Chem. Asian J. 2018, 13, 2378-2381.
 
For the concept of ACDC, see: S. Mayer, B. List, Angew. Chem. Int. Ed. 2006, 45, 4193-4195;
Angew. Chem. 2006, 118, 4299-4301;
R. J. Phipps, G. L. Hamilton, F. D. Toste, Nat. Chem. 2012, 4, 603-614;
M. Mahlau, B. List, Angew. Chem. Int. Ed. 2013, 52, 518-533;
Angew. Chem. 2013, 125, 540-556.
 
For pioneering work on ACDC using transition metals, see: G. L. Hamilton, E. J. Kang, M. Mba, F. D. Toste, Science 2007, 317, 496-499;
S. Mukherjee, B. List, J. Am. Chem. Soc. 2007, 129, 11336-11337.
 
For selected general reviews on the transient directing group approach in C−H functionalization, see: D. S. Kim, W. J. Park, C. H. Jun, Chem. Rev. 2017, 117, 8977-9015;
P. Gandeepan, L. Ackermann, Chem 2018, 4, 199-222.
F.-L. Zhang, K. Hong, T.-J. Li, H. Park, J.-Q. Yu, Science 2016, 351, 252-256.
G. Li, J. Jiang, H. Xie, J. Wang, Chem. Eur. J. 2019, 25, 4688-4694.

Auteurs

Tatsuhiko Yoshino (T)

Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-ku, Sapporo, 060-0812, Japan.

Shun Satake (S)

Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-ku, Sapporo, 060-0812, Japan.

Shigeki Matsunaga (S)

Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-ku, Sapporo, 060-0812, Japan.

Classifications MeSH