10.1002/adsc.201801713
Advanced Synthesis & Catalysis
COMMUNICATION
Rueping, Chem. Commun. 2015, 51, 1937–1940; c) J.-L. Tao, Z.-X.
Wang, Asian J. Org. Chem. 2016, 5, 521–527; d) D. Heijnen, J.-B.
Gualtierotti, V. Hornillos, B. L. Feringa, Chem. Eur. J. 2016, 22, 3991–
3995; e) Z.-K. Yang, D.-Y. Wang, H. Minami, H. Ogawa, T. Ozaki, T.
Saito, K. Miyamoto, C. Wang, M. Uchiyama, Chem. Eur. J. 2016, 22,
15693–15699; f) Y. A. Ho, M. Leiendecker, X. Liu, C. Wang, N. Alandini,
M. Rueping, Org. Lett. 2018, 20, 5644–5647. For polymerization, see: g)
S. B. Jhaveri, J. J. Peterson, K. R. Carter, Macromolecules 2008, 41,
8977–8979; h) K. Fuji, S. Tamba, K. Shono, A. Sugie, A. Mori, J. Am.
Chem. Soc. 2013, 135, 12208–12211; i) Z.-K. Yang, N.-X. Xu, R. Takita,
A. Muranaka, C. Wang, M. Uchiyama, Nat. Commun. 2018, 9, 1587. For
homocoupling, see: j) S. B. Jhaveri, K. R. Carter, Chem. Eur. J. 2008,
14, 6845–6848.
Keywords: nickel • cross-coupling • organolithium • bisphosphine
• heterogeneous catalyst
References
[1]
[2]
Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F.
Diederich), Willy-VCH: Weinheim, Germany, 2004.
a) S.-I. Murahashi, Y. Tanba, M. Yamamura, I. Moritani, Tetrahedron Lett.
1974, 15, 3749–3752; b) M. Yamamura, I. Moritani, S.-I. Murahashi, J.
Organomet. Chem. 1975, 91, C39–C42; c) S.-I. Murahashi, M.
Yamamura, K.-I. Yanagisawa, N. Mita, K. Kondo, J. Org. Chem. 1979,
44, 2408–2417; d) S.-I. Murahashi, J. Organomet. Chem. 2002, 653, 27–
33.
[9]
Recently, the iron-catalyzed cross-coupling using organolithiums was
reported. Z. Jia, Q. Liu, X.-S. Peng, H. N. C. Wong, Nat. Commun. 2016,
7, 10614.
[3]
a) M. Giannerini, M. Fañanás-Mastral, B. L. Feringa, Nat. Chem. 2013,
5, 667–672; b) V. Hornillos, M. Giannerini, C. Vila, M. Fañanás-Mastral,
B. L. Feringa, Org. Lett. 2013, 15, 5114–5117; c) M. Giannerini, V.
Hornillos, C. Vila, M. Fañanás-Mastral, B. L. Feringa, Angew. Chem.
2013, 125, 13571–13575; Angew. Chem. Int. Ed. 2013, 52, 13329–
13333; d) C. Vila, M. Giannerini, V. Hornillos, M. Fañanás-Mastral, B. L.
Feringa, Chem. Sci. 2014, 5, 1361–1367; e) C. Vila, V. Hornillos, M.
Giannerini, M. Fañanás-Mastral, B. L. Feringa, Chem. Eur. J. 2014, 20,
13078–13083; f) V. Hornillos, M. Giannerini, C. Vila, M. Fañanás-Mastral,
B. L. Feringa, Chem. Sci. 2015, 6, 1394–1398; g) L. M. Castellꢀ, V.
Hornillos, C. Vila, M. Giannerini, M. Fañanás-Mastral, B. L. Feringa, Org.
Lett. 2015, 17, 62–65; h) D. Heijnen, V. Hornillos, B. P. Corbet, M.
Giannerini, B. L. Feringa, Org. Lett. 2015, 17, 2262–2265; i) M.
Giannerini, C. Vila, V. Hornillos, B. L. Feringa, Chem. Commun. 2016,
52, 1206–1209; j) E. B. Pinxterhuis, M. Giannerini, V. Hornillos, B. L.
Feringa, Nat. Commun. 2016, 7, 11698; k) D. Heijnen, F. Tosi, C. Vila,
M. C. A. Stuart, P. H. Elsinga, W. Szymanski, B. L. Feringa, Angew.
Chem. 2017, 129, 3402–3407; Angew. Chem. Int. Ed. 2017, 56, 3354–
3359. For homocoupling, see: l) J. Buter, D. Heijnen, C. Vila, V. Hornillos,
E. Otten, M. Giannerini, A. J. Minnaard, B. L. Feringa, Angew. Chem.
2016, 128, 3684–3688; Angew. Chem. Int. Ed. 2016, 55, 3620–3624.
a) The Chemistry of Organolithium Compounds (Eds.: Z. Rappoport, I.
Marek), Wiley-VCH, Weinheim 2004; b) Lithium Compounds in Organic
Synthesis (Eds.: R. Luisi, V. Capriati), Wiley-VCH, Weinheim 2014.
For selected reviews for cross-coupling reactions using organolithiums,
see: a) V. Pace, R. Luisi, ChemCatChem 2014, 6, 1516–1519; b) V.
Capriati, F. M. Perna, A. Salomone, Dalton Trans. 2014, 43, 14204–
14210; c) J. D. Firth, P. O’Brien, ChemCatChem 2015, 7, 395–397.
For application of micro flow chemistry to Pd-catalyzed cross-coupling
using organolithiums, see: A. Nagaki, A. Kenmoku, Y. Moriwaki, A.
Hayashi, J. Yoshida, Angew. Chem. 2010, 122, 7705–7709; Angew.
Chem. Int. Ed. 2010, 49, 7543–7547.
[10] T. Iwai, T. Harada, H. Shimada, K. Asano, M. Sawamura, ACS Catal.
2017, 7, 1681–1692.
[11] R. Jana, T. P. Pathak, M. S. Sigman, Chem. Rev. 2011, 111, 1417–1492.
[12] J.-R. Wang, K. Manabe, Org. Lett. 2009, 11, 741–744.
[13] 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.
[14] The Ni loading value of [NiCl2(PS-DPPBz)] had deviations depending on
determination methods. Elemental analysis of Cl or P for [NiCl2(PS-
DPPBz)] indicated that the Ni loading to the polystyrene resin was
estimated to be 0.093 or 0.094 mmol/g, respectively, based on the Ni to
Cl or P stoichiometry of 1:2. These values were underestimated as
compared to the value of the DPPBz moiety of PS-DPPBz calculated by
elemental analysis of P (0.12 mmol/g, see ref 10). Thus, this calculated
value (0.12 mmol/g) was used as the Ni loading in this study, assuming
that the ratio of Ni to the DPPBz moiety was equal. See Supporting
Information for characterization details.
[15] A comprehensive study of coordination properties of bisphosphines
toward [Ni(cod)2]: A. L. Clevenger, R. M. Stolley, N. D. Staudaher, N. Al,
A. L. Rheingold, R. T. Vanderlinden, J. Louie, Organometallics 2018, 37,
3259–3268.
[4]
[5]
[16] Selected reviews on cross-coupling of aryl ethers: a) J. Cornella, C.
Zarate, R. Martin, Chem. Soc. Rev. 2014, 43, 8081–8097; b) M. Tobisu,
N. Chatani, Acc. Chem. Res. 2015, 48, 1717–1726. See also refs
8a,b,d,e,i for C–O cross-coupling with organolithiums.
[17] For oxidative addition of aryl electrophiles to a Ni(0) complex, see: S.
Bajo, G. Laidlaw, A. R. Kennedy, S. Sproules, D. J. Nelson,
Organometallics 2017, 36, 1662–1672.
[6]
[7]
[18] V. Snieckus, Chem. Rev. 1990, 90, 879–933.
[19] Rueping et al. reported the Ni-catalyzed cross-coupling reactions of
Me3SiCH2Li via C–O or C–F bond cleavage. See refs 8a,b,f.
[20] The [NiCl2(PS-DPPBz)] catalyst system was applicable to the reactions
of aryllithiums. Specifically, the reaction between 1a and PhLi (1.09 M in
cyclohexane/Et2O, 1.5 eq) with 1 mol% of [NiCl2(PS-DPPBz)] in hexane
For representative examples of Pd-catalyzed cross-coupling reactions
using organolithiums, see: a) Y. Kobayashi, M. Nakamoto, Y. Inagaki, A.
Sekiguchi, Angew. Chem. 2013, 125, 10940–10944; Angew. Chem. Int.
Ed. 2013, 52, 10740–10744; b) Y. Kitazawa, M. Otsuka, J. Kanazawa,
R. Takita, M. Uchiyama, Synlett 2015, 26, 2403–2407; c) J.-Y. Lu, H.
Wan, J. Zhang, Z. Wang, Y. Li, Y. Du, C. Li, Z.-T. Liu, Z.-W. Liu, J. Lu,
Chem. Eur. J. 2016, 22, 17542–17546.
(0.5 M) at 40 °C for 24
h without slow addition produced the
corresponding biaryl compound (2-phenylnaphthalene, 3s) in 48% NMR
yield (68% conv. of 1a), which was comparable to that with the Feringa’s
catalyst [NiCl2(IPr)(PPh3)] (ref 8d) under otherwise the same conditions
(69% conv., 53% yield). The reaction using 2-thienyllithium (1.0 M in
THF/hexane, 1 mol% Ni, 25 °C, 5 h) gave 2-(2-naphthyl)thiophene (3t)
in 32% isolated yield.
[8]
a) M. Leiendecker, C.-C. Hsiao, L. Guo, N. Alandini, M. Rueping, Angew.
Chem. 2014, 126, 13126–13129; Angew. Chem. Int. Ed. 2014, 53,
12912–12915; b) L. Guo, M. Leiendecker, C.-C. Hsiao, C. Baumann, M.
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