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Chemical Science
Edge Article
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Aldrichimica Acta, 2004, 37, 87.
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Colacot and V. Snieckus, Angew. Chem. Int. Ed., 2012, 51, 16 (a) For a review, see: J. Schwarz and B. König, Green Chem.,
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2018, 20, 323 and references cited therein; (b) For additional
examples, see: refs. 9-10 and references cited therein; For
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4114; (d) A. Zapf, Angew. Chem. Int. Ed., 2003, 42, 5394; (e)
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A. Dey, S. Sasmai, K. Seth, G. K. Lahiri and D. Maiti, ACS
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H. Yue, L. Guo, S. C. Lee, X. Liu and M. Rueping, Angew.
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Gooßen, Angew. Chem. Int. Ed., 2008, 47, 3100.
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0 For additional reviews, see: (a) N. Rodriguez and L. J.
Gooßen, Chem. Soc. Rev., 2011, 40, 5030; (b) W. Dzik, P.
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18 For selected recent reviews, see: (a) C. N. Neumann and T.
Ritter, Acc. Chem. Res., 2017, 50, 2822; (b) K. N. Lee, J. W.
Lee and M. Y. Ngai, Tetrahedron, 2018, 74, 7127.
1 For recent reviews on decarbonylative cross-couplings, see:
(a) C. Liu and M. Szostak, Org. Biomol. Chem., 2018, 16,
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998; (b) L. Guo and M. Rueping, Acc. Chem. Res., 2018, 51, 19 L. Huang and D. J. Weix, Org. Lett., 2016, 18, 5432.
185; (c) A. Dermenci and G. Dong, Sci. China Chem., 2013, 20 J. Mortier, Arene Chemistry: Reaction Mechanisms and
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1, 327; For selected mechanistic studies on 21 (a) M. Garcia-Melchor, A. A. C. Braga, A. Lledos, G. Ujaque
decarbonylation, see: (e) P. Fristrup, M. Kreis, A. Palmelund,
P. O. Norrby and R. Madsen, J. Am. Chem. Soc., 2008, 130,
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and F. Maseras, Acc. Chem. Res., 2013, 46, 2626; (b) A.
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22 For selected computational studies of oxidative addition with
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Hermann and W. Thiel, Organometallics, 2005, 24, 2398; (b)
M. Ahlquist, P. Fristrup, D. Tanner and P. O. Norrby,
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Marder and Z. Lin, Organometallics, 2007, 26, 758; (e) T. E.
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2 For selected decarbonylative cross-couplings from our
groups, see: (a) G. Meng and M. Szostak, Angew. Chem. Int.
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Angew. Chem. Int. Ed., 2016, 55, 6959; (c) G. Meng and M.
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Am. Chem. Soc., 2017, 139, 15522; (h) C. Liu, C. L. Ji, X. Hong
and M. Szostak, Angew. Chem. Int. Ed., 2018, 57, 16721.
3 For selected recent examples of decarbonylative and
decarboxylative cross-coupling reactions, see: (a) S. T.
Keaveney and F. Schoenebeck, Angew. Chem. Int. Ed., 2018,
23 For a computational study of decarbonylation with palladium
catalysis, see: M. Lesslie, Y. Yang, A. J. Canty, E. Piacentino, F.
Berthias, P. Maitre, V. Ryzhov and R. A. J. OHair, Chem.
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7, 4073; (b) A. Chatupheeraphat, H. H. Liao, W. Srimontree, 24 For a computational study of reductive elimination with
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M. Garcia-Melchor, M. H. Pérez-Temprano, J. A. Casares, G.
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Love, Chem. Soc. Rev., 2017, 46, 197; (e) K. Muto, J. 25 Q. Zhao and M. Szostak, ChemSusChem, 2019, 12, DOI:
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, 7508; (f) C. Liu and M. Szostak, Chem. Commun., 2018, 54,
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Doyle and D. W. C. MacMillan, Science, 2014, 345, 437; (h) D.
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007, 129, 11750.
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4 For further recent examples demonstrating the utility of
decarbonylative manifold, see: (a) S. K. Murphy, J. W. Park, F.
A. Cruz and V. M. Dong, Science, 2015, 347, 56; (b) J. Hu, Y.
Zhao, J. Liu, Y. Zhang and Z. Shi, Angew. Chem. Int. Ed., 2016,
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5, 8718; (c) X. Fang, B. Cacherat and B. Morandi, Nat.
Chem., 2017, 9, 1105; (d) M. De La Higuera Macias and B. A.
Arndtsen, J. Am. Chem. Soc., 2018, 140, 10140; (e) Y. H. Lee
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J. R. Bour, C. E. Brigham and M. S. Sanford, Nature, 2018,
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63, 100.
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5 (a) For a recent review on reactions of thioesters, including
decarbonylations, see: V. Hirschbeck, P. H. Gehrtz and I.
Fleischer, Chem. Eur. J., 2018, 24, 7092; For a review on
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