Communication
ChemComm
2 Transition Metals for Organic Synthesis, ed. M. Beller and C. Bolm,
Wiley-VCH, Weinheim, 2004.
9 M. V. Joannou, M. J. Bezdek, K. Albahily, I. Korobkov and P. J. Chirik,
Organometallics, 2018, 37, 3389–3393.
3 Metal-Catalyzed Cross-Coupling Reactions, ed. A. de Meijere and 10 For a report on characterization by ESR of NiI(PEt3)3 at g = 2.180, see:
F. Diederich, Wiley-VCH, Weinheim, 2004. T. T. Tsou and J. K. Kochi, J. Am. Chem. Soc., 1979, 101, 6319–6332.
4 D. A. Petrone, J. Ye and M. Lautens, Chem. Rev., 2016, 116, 8003–8104. 11 (a) P. T. Matsunaga, G. L. Hillhouse and A. L. Rheingold, J. Am.
5 (a) A. H. Roy and J. F. Hartwig, J. Am. Chem. Soc., 2001, 123, 1232–1233;
(b) A. H. Roy and J. F. Hartwig, J. Am. Chem. Soc., 2003, 125,
13944–13945; (c) J. F. Hartwig, Inorg. Chem., 2007, 46, 1936–1947.
6 For examples of Pd-catalyzed carbohalogenations of alkynes, see:
(a) C. M. Le, P. J. C. Menzies, D. A. Petrone and M. Lautens, Angew.
Chem. Soc., 1993, 115, 2075–2077; (b) P. T. Matsunaga, J. C.
Mavropoulos and G. L. Hillhouse, Polyhedron, 1995, 14, 175–185;
(c) R. Han and G. L. Hillhouse, J. Am. Chem. Soc., 1997, 119,
8135–8136; (d) J. A. Terrett, J. D. Cuthbertson, V. Shurtleff and
D. W. C. MacMillan, Nature, 2015, 524, 330–334.
Chem., Int. Ed., 2015, 54, 254–257; for a mechanistic report, see: 12 The stoichiometric experiment using Ni(0)/dtbpy, iodobenzne
(b) T. Sperger, C. M. Le, M. Lautens and F. Schoenebeck, Chem. Sci.,
2017, 8, 2914–2922.
7 (a) D. R. Heitz, J. C. Tellis and G. A. Molander, J. Am. Chem. Soc.,
(2 equiv.) and 4-octyne (3 equiv.) resulted in formation of product
in 33% yield. These results also supported the formation of Ni(I) via
comproportionation.
2016, 138, 12715–12718; (b) X. Zhang and D. W. C. MacMillan, J. Am. 13 For representative examples of comproportionation of Ni(0)/Ni(II) in
˜
Chem. Soc., 2016, 138, 13862–13865; (c) V. B. Phapale, E. Bunuel,
catalytic reaction, see: (a) I. Kalvet, Q. Guo, G. J. Tizzard and
F. Schoenebeck, ACS Catal., 2017, 7, 2126–2132; (b) A. B. Du¨rr,
H. C. Fisher, I. Kalvet, K.-N. Truong and F. Schoenebeck, Angew. Chem.,
Int. Ed., 2017, 56, 13431–13445; (c) K. Matsubara, Y. Fukahori,
T. Inatomi, S. Takazaki, Y. Koga, S. Kanegawa and T. Nakamura,
Organometallics, 2016, 35, 3281–3287; (d) A. Velian, S. Lin,
A. J. M. Miller, M. W. Day and T. Agapie, J. Am. Chem. Soc., 2010,
132, 6296–6297; (e) R. Beck and S. A. Johnson, Organometallics, 2013,
32, 2944–2951; ( f ) R. Beck, M. Shoshani, J. Krasinkiewicz, J. A.
Hatnean and S. A. Johnson, Dalton Trans., 2013, 42, 1461–1475;
(g) A. Velian, S. Lin, A. J. M. Miller, M. W. Day and T. Agapie, J. Am.
Chem. Soc., 2010, 132, 6296–6297.
´
´
M. Garcıa-Iglesias and D. J. Cardenas, Angew. Chem., Int. Ed., 2007,
46, 8790–8795; (d) D. A. Everson, R. Shrestha and D. J. Weix, J. Am.
Chem. Soc., 2010, 132, 920–921; (e) A. Garcıa-Domınguez, Z. Li and
´
´
¨
C. Nevado, J. Am. Chem. Soc., 2017, 139, 6835–6838; ( f ) M. Borjesson,
T. Moragas and R. Martin, J. Am. Chem. Soc., 2016, 138, 7504–7507;
(g) T. Qin, J. Cornella, C. Li, L. R. Malins, J. T. Edwards, S. Kawamura,
B. D. Maxwell, M. D. Eastgate and P. S. Baran, Science, 2016, 352,
801–805; (h) A. Klein, A. Kaiser, W. Wielandt, F. Belaj, E. Wendel,
´ ˇ
H. Bertagnolli and S. Zalis, Inorg. Chem., 2008, 47, 11324–11333;
(i) S. Biswas and D. J. Weix, J. Am. Chem. Soc., 2013, 135, 16192–16197;
( j) K. Nakajima, S. Nojima and Y. Nishibayashi, Angew. Chem.,
Int. Ed., 2016, 55, 14106–14110.
8 For mechanistic reports on radical-like reactivity of Ni/bpy, see:
(a) B. J. Shields, B. Kudisch, G. D. Scholes and A. G. Doyle, J. Am.
14 An addition of TEMPO radical scavenger retarded the reaction.
Radical probe experiment with acetylene bearing two cyclopropyl
group resulted in formation of product in trace yield.
Chem. Soc., 2018, 140, 3035–3039; (b) B. J. Shields and A. G. Doyle, 15 For a selected review, see: S. Z. Tasker, E. A. Standley and T. F. Jamison,
J. Am. Chem. Soc., 2016, 138, 12719–12722.
Nature, 2014, 509, 299–309.
This journal is ©The Royal Society of Chemistry 2018
Chem. Commun., 2018, 54, 12750--12753 | 12753