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Chemical Science
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Journal Name
ARTICLE
relevant to the design of various new approaches to
carbonylative C-H bond functionalization chemistry.
10601; g) D. Willcox, B. G. N. ChappelDl,OKI:. 1F0..1H0o39g/gD,0JS.CC0a0l0le8j5aJ,
A. P. Smalley, M. J. Guant, Science 2016, 354, 851-857.
Q. Liu, H. Zhang, A. Lei, Angew. Chem. Int. Ed. 2011, 50,
10788-10799.
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Conflicts of interest
There are no conflicts to declare.
a) M. A. Campo, R. C. Larock, J. Org. Chem. 2002, 67, 5616-
5620; b) X.-F. Wu, P. Anbarasan, H. Neumann, M. Beller,
Angew. Chem. Int. Ed. 2010, 49, 7316-7319; c) Z. Lian, S. D.
Friis, T. Skrydstrup, Chem. Commun, 2015, 51, 1870-1873; d)
J. Liu, Z. Wei, H. Jiao, R. Jackstell, M. Beller, ACS Cent. Sci.
2018, 4, 30-38; e) T. A. Cernak, T. H. Lambert, J. Am. Chem.
Soc. 2009, 131, 3124-3125; f) F. Zeng, H. Alper, Org. Lett.
2013, 15, 2034-2037.
a) H. Zhang, R. Shi, P, Gan, C. Liu, A. Ding, Q. Wang, A. Lei,
Angew. Chem. Int. Ed. 2012, 51, 5204-5207; b) J. Wen, S.
Tang, F. Zhang, R. Shi, A. Lei, Org. Lett. 2017, 19, 94-97.
a) X.-F. Wu, H. Neumann, M. Beller, Chem. Soc. Rev. 2011,
40, 4986-5009; b) M.-N. Zhao, L. Ran, M. Chen, Z.-H. Ren, Y.-
Y. Wang, Z.-H. Guan, ACS Catal. 2015, 5, 1210-1213.
Acknowledgements
We thank NSERC, the Canadian Foundation for Innovation
(CFI), the McGill Sustainability Systems Initiative (MSSI)
through the Ideas Fund, and the FQRNT supported Centre for
Green Chemistry and Catalysis for funding this research.
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Notes and references
10 For an alternative approach from aldehydes: a) S. Tetsuya, I.
Tomoaki, M. Masahiro, N. Masakatsu, Chem. Lett. 1996, 25,
823-824; b) S. Ko, B. Kang, S. Chang, Angew. Chem. Int. Ed.
2005, 44, 455-457; c) J. Ruan, O. Saidi, J. A. Iggo, J. Xiao, J.
Am. Chem. Soc. 2008, 130, 10510-10511; d) X. Jia, S. Zhang,
W. Wang, F. Luo, J. Cheng, Org. Lett. 2009, 11, 3120-3123. e)
P. Álvarez-Bercedo, A. Flores-Gaspar, A. Correa, R. Martin, J.
Am. Chem. Soc. 2010, 132, 466-467; f) B. Suchand, G.
Satyanarayana, J. Org. Chem. 2016, 81, 6409-6423; g) T.
Wakaki, T. Togo, D. Yoshidome, Y. Kuninobu, M. Kanai, ACS
Catal. 2018, 8, 3123-3128.
11 a) J. S. Quesnel, B. A. Arndtsen, J. Am. Chem. Soc. 2013, 135,
16841-16844; b) J. S. Quesnel, L. V. Kayser, A. Fabrikant, B. A.
Arndtsen, Chem. Eur. J. 2015, 21, 9550-9555; c) J. Tjutrins, B.
A. Arndtsen, J. Am. Chem. Soc. 2015, 137, 12050-12054; d) R.
G. Kinney, J. Tjutrins, G. M. Torres, N. J. Liu, O. Kulkarni, B. A.
Arndtsen, Nat. Chem. 2018, 10, 193-199; e) P.-L. Lagueux-
Tremblay, A. Fabrikant, B. A. Arndtsen, ACS Catal. 2018, 8,
5350-5354.
12 a) J. Tsuji, Acc. Chem. Res. 1969, 2, 144-152; b) J. Tsuji,
Palladium Reagents and Catalysts – New Perspectives for the
21st Century, John Wiley & Sons Ltd., West Sussex, 2004; c)
C. F. J. Barnard, Organometallics 2008, 27, 5402-5422; d) X.-
F. Wu, H. Neumann, A. Spannenberg, T. Schulz, H. Jiao, M.
Beller, J. Am. Chem. Soc. 2010, 132, 14596-14602.
13 PdCl2 has been suggested to react with CO to generate
phosgene derivatives. a) T. A. Stromnova, M. N. Vargaftik, I.
I. Moiseev, J. Organomet. Chem. 1983, 252, 113-120; b) D. B.
Dell’Amico, F. Calderazzo, N. Zandona, Inorg. Chem. 1984,
23, 137-140; c) S. Baig, B. Richard, P. Serp, C. Mijoule, K.
Hussein, N. Guihéry, J.-C. Barthelat, P. Kalck, Inorg. Chem.
2006, 45, 1935-1944; d) F. Ragaini, H. Larici, M. Rimoldi, A.
Caselli, F. Ferretti, P. Macchi, N. Casati, Organometallics
2011, 30, 2385-2393.
14 The reaction proceeds well with a near stoichiometric
amount of arene (2.1 : 1 arene to I2 ratio, entry 10), but we
observed slightly elevated yields with 1.5 equiv. of arene (3 :
1 ratio of arene to I2).
15 For mechanistic studies with related transition metal
acetates: a) D. Lapointe, K. Fagnou, Chem. Lett. 2010, 39,
1118-1126; b) S. I. Gorelsky, Coord. Chem. Rev. 2013, 257,
153-164; c) L. Wang, B. P. Carrow, ACS Catal. 2019, 9, 6821-
6836; d) D. Whitaker, J. Burés, I. Larrosa, J. Am. Chem. Soc.
2016, 138, 8384-8387; e) S. Y. Lee, J. F. Hartwig, J. Am. Chem.
Soc. 2016, 138, 15278-15284; f) M. D. Lotz, N. M. Camasso,
A. J. Canty, M. S. Sanford, Organometallics 2017, 36, 165-
171; g) C. Colletto, A. Panigrahi, J. Fernández-Casado, I.
Larrosa, J. Am. Chem. Soc. 2018, 140, 9638-9643.
1
For reviews: a) J. F. Hartwig, J. Am. Chem. Soc. 2016, 138, 2-
24; b) T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110,
1147-1169; c) X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu,
Angew. Chem. Int. Ed. 2009, 48, 5094-5115; d) T. Cernak, K.
D. Dykstra, S. Tyagarajan, P. Vachal, S. W. Krska, Chem. Soc.
Rev. 2016, 45, 546-576; e) J. F. Hartwig, M. A. Larsen, ACS
Cent. Sci. 2016, 2, 281-292; f) P. Gandeepan, T. Müller, D.
Zell, G. Cera, S. Warratz, L. Ackermann, Chem. Rev. 2019,
119, 2192-2452; g) O. Daugulis, H.-Q. Do, D. Shabashov, Acc.
Chem. Res. 2009, 42, 1074-1086; h) P. Wedi, M. van
Gemmeren, Angew. Chem. Int. Ed. 2018, 57, 13016-13027.
a) C. Liu, J. Yuan, M. Gao, S. Tang, W. Li, R. Shi, A. Lei, Chem.
Rev. 2015, 115, 12138-12204; b) Y. Yang, J. Lan, J. You, Chem.
Rev. 2017, 117, 8787-8863; c) C. S. Yeung, V. M. Dong, Chem.
Rev. 2011, 111, 1215-1292; d) Y.-F. Zhang, Z.-J. Shi, Acc.
Chem. Res. 2019, 52, 161-169; e) J. A. Ashenhurst, Chem.
Soc. Rev. 2010, 39, 540-548; f) C.-J. Li, Acc. Chem. Res. 2009,
42, 335-344.
For representative examples: a) R. Li, L. Jiang, W. Lu,
Organometallics 2006, 25, 5973-5975; b) X. Wang, D. Leow,
J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 13864-13867; c) D. R.
Stuart, K. Fagnou, Science 2007, 316, 1172-1175; d) T. W.
Lyons, K. L. Hull, M. S. Sanford, J. Am. Chem. Soc. 2011, 133,
4455-4464; e) K. Kawasumi, K. Mochida, T. Kajino, Y. Segawa,
K. Itami, Org. Lett. 2012, 14, 418-421; f) X. Zhao, C. S. Yeung,
V. M. Dong, J. Am. Chem. Soc. 2010, 132, 5837-5844; g) G.
Brasche, J. García-Fortanet, S. L. Buchwald, Org. Lett. 2008,
10, 2207-2210; h) K. Matsumoto, S. Takeda, T. Hirokane, M.
Yoshida, Org. Lett. 2019, 21, 7279-7283; i) D. Wang, S. S.
Stahl, J. Am. Chem. Soc. 2017, 139, 5704-570; j) B.-J. Li, S.-L.
Tian, Z. Fang, Z.-J. Shi, Angew. Chem. Int. Ed. 2008, 47, 1115-
1118; k) Y. Wei, W. Su, J. Am. Chem. Soc. 2010, 132, 16377-
16379; l) C.-Y. He, S. Fan, X. Zhang, J. Am. Chem. Soc. 2010,
132, 12850-12852.
2
3
4
5
a) M. Beller, X.-F. Wu, Transition Metal Catalyzed
Carbonylations-Carbonylative Activation of C-X Bonds,
Springer, Berlin, 2013; b) Y. Li, Y. Hu, X.-F. Wu, Chem. Soc.
Rev. 2018, 47, 172-194; c) A. Brennführer, H. Neumann, M.
Beller, Angew. Chem. Int. Ed. 2009, 48, 4114-4133; d) I.
Omae, Coord. Chem. Rev. 2011, 255, 139-160.
For reviews see: a) C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem.
Res. 2001, 34, 633-639; For recent examples: b) K. Orito, A.
Horibata, T. Nakamura, H. Ushito, H. Nagasaki, M. Yuguchi, S.
Yamashita, M. Tokuda, J. Am. Chem. Soc. 2004, 126, 14342-
14343; c) R. Giri, J.-Q. Yu, J. Am. Chem. Soc. 2008, 130,
14082-14083; d) R. Giri, J. K. Lam, J.-Q. Yu, J. Am. Chem. Soc.
2010, 132, 686-693; e) Z.-H. Guan, M. Chen, Z.-H. Ren, J. Am.
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