ACS Catalysis
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(2) For selected examples, see: (a) Dyker, G. Palladium-
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Hepburn, H. B.; Lam, H. W. The Isomerization of Allylrhodium
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Sawano, T.; Hashizume, M.; Nishimoto, S.; Ou, K.; Nishimura, T.
Formation of Carbocycles via a 1,4-Rh Shift Triggered by a
Rhodium-Catalyzed Addition of Terminal Alkynes to 3,3-
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Hayashi, T. Aryloxymethyltrifluoroborates for Rhodium-Catalyzed
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Callingham, M.; Lewis, W.; Lam, H. W. Arylative Intramolecular
Allylation of Ketones with 1,3-Enynes Enabled Catalytic Alkenyl-
to-Allyl 1,4-Rhodium(I) Migration. Angew. Chem., Int. Ed. 2017, 56,
7227–7232. (i) Callingham, M.; Partridge, B. M.; Lewis, W.; Lam, H.
W. Enantioselective Rhodium-Catalyzed Coupling of Arylboronic
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Zhang, S.-S.; Hu, T.-J.; Li, M.-Y.; Song, Y.-K.; Yang, X.-D.; Feng, C.-G.;
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(5) For examples of 1,4-rhodium(III) migration, see: (a) Ikeda,
Y.; Takano, K.; Kodama, S.; Ishii, Y. 1,4-Metal Migration in a
Cp*Rh(III) Complex. Chem. Commun. 2013, 49, 11104–11106. (b)
Ikeda, Y.; Takano, K.; Waragai, M.; Kodama, S.; Tsuchida, N.; Takano,
K.; Ishii, Y. Reversibility of 1,4-Metal Migration in a Cp*RhIII and
Cp*IrIII Complexes. Organometallics 2014, 33, 2142–2145. (c)
Burns, D. J.; Lam, H. W. Catalytic 1,4-Rhodium(III) Migration
Enables 1,3-Enynes to Function as One-Carbon Oxidative
Annulation Partners in C–H Functionalizations. Angew. Chem., Int.
Ed. 2014, 53, 9931–9935. (d) Burns, D. J.; Best, D.; Wieczysty, M. D.;
Lam, H. W. All-Carbon [3+3] Oxidative Annulations of 1,3-Enynes
by Rhodium(III)-Catalyzed C–H Functionalization and 1,4-
Migration. Angew. Chem., Int. Ed. 2015, 54, 9958–9962. (e) Korkis,
S. E.; Burns, D. J.; Lam, H. W. Rhodium-Catalyzed Oxidative C–H
Allylation of Benzamides with 1,3-Dienes by Allyl-to-Allyl 1,4-
Rh(III) Migration. J. Am. Chem. Soc. 2016, 138, 12252–12257. (f)
Dooley, J. D.; Lam, H. W. One-Carbon Oxidative Annulations of 1,3-
Enynes by Catalytic C–H Functionalization and 1,4-Rhodium(III)
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(3) For examples of 1,4-rhodium(I) migration from
alkenylrhodium intermediate to sp2-carbon, see: (a) Hayashi, T.;
Inoue, K.; Taniguchi, N.; Ogawawara, M. Rhodium-Catalyzed
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Rhodium from 2-Aryl-1-alkenylrhodium to 2-Alkenylarylrhodium
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1391. (d) Yamabe, H.; Mizuno, A.; Kusama, H.; Iwasawa, N. Rh(I)-
Catalyzed Cyclization of 1-Arylprop-2-yn-1-ol Derivatives Utilizing
Rhodium 1,4-Migration. J. Am. Chem. Soc. 2005, 127, 3248–3249.
(e) Shintani, R.; Takatsu, K.; Hayashi, T. Rhodium-Catalyzed
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Chem., Int. Ed. 2007, 46, 3735–3737. (f) Shintani, R.; Isobe, S.;
Takeda, M.; Hayashi, T. Rhodium-Catalyzed Asymmetric Synthesis
of Spirocarbocycles: Arylboron Reagents as Surrogates of 1,2-
Dimetalloarenes. Angew. Chem., Int. Ed. 2010, 49, 3795–3798. (g)
Claraz, A.; Serpier, F.; Darses, S. Organoboron Initiated Rh-
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Regioselectivity Leading to Chiral 3-Benzazepine Derivatives. ACS
Catal. 2017, 7, 3410–3413. (h) Ming, J.; Hayashi, T. Rhodium-
Catalyzed Arylzincation of Alkynes: Ligand Control of 1,4-
Migration Selectivity. Org. Lett. 2018, 20, 6188–6192. (i) Ming, J.;
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(6) Partridge, B. M.; González, J. S.; Lam, H. W. Iridium-Catalyzed
Arylative Cyclization of Alkynones by 1,4-Iridium Migration.
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(7) (a) Tan, B.-H.; Dong, J.; Yoshikai, N. Cobalt-Catalyzed Addition
of Arylzinc Reagents to Alkynes to Form ortho-Alkenylarylzinc
Species through 1,4-Cobalt Migration. Angew. Chem., Int. Ed. 2012,
51, 9610–9614. (b) Wu, B.; Yoshikai, N. Versatile Synthesis of
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Cyclization of Acetylenic Esters and Ketones with Arylzinc
Reagents through 1,4-Cobalt Migration. ACS Catal. 2016, 6, 3738–
3742.
(8) (a) Yan, J.; Yoshikai, N. Chromium-Catalyzed Migratory
Arylmagnesiation of Unactivated Alkynes. Org. Chem. Front. 2017,
4, 1972–1975. (b) Yan, J.; Yoshikai, N. Phenanthrene Synthesis via
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(9) Keen, A. L.; Doster, M.; Johnson, S. A. 1,4-Shifts in a Dinuclear
Ni(I) Biarylyl Complex: A Mechanistic Study of C–H Bond
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ortho-Alkenylarylstannanes Catalysed Cooperatively by
a
Rhodium Complex and Zinc Chloride. Chem. Sci. 2018, 9, 7700–
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(4) For other types of 1,4-rhodium(I) migration, see: (a) Oguma,
K.; Miura, M.; Satoh, T.; Nomura, M. Merry-Go-Round Multiple
Alkylation on Aromatic Rings via Rhodium Catalysis. J. Am. Chem.
Soc. 2000, 122, 10464–10465. (b) Seiser, T.; Roth, O. A.; Cramer, N.
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Chem., Int. Ed. 2009, 48, 6320–6323. (c) Matsuda, T.; Suda, Y.;
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Arylcyclobutylidene)acetates. Chem. Commun. 2012, 48, 2988–
2990. (d) Shintani, R.; Iino, R.; Nozaki, K. Rhodium-Catalyzed
(10) Singh, A.; Sharp, P. R. Pt and Pd 1,4-Shifts at the Edge of
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