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ACS Catalysis
ASSOCIATED CONTENT
Supporting Information
Metallic Reducing Agents. Synthesis 2018, 50, 499. (h) Ananikov, V. P.
Nickel: The “Spirited Horse” of Transition Metal Catalysis. ACS. Catal.
015, 5, 1964. (i) Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Recent Ad-
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vances in Homogeneous Nickel Catalysis. Nature 2014, 509, 299.
Instrumentation and chemicals, optimization of reaction condition,
experimental procedure and characterization data for products,
NMR spectra and Chiral HPLC conditions, total synthesis proce-
dure and characterization.
(3) For Examples of Pd-Catalyzed Carboiodination see: (a) Zhang, Z.-M.;
Xu, B.; Wu, L.; Zhou, L.; Ji, D.; Liu, Y.; Li, Z.; Zhang, J. Palla-
dium/XuPhos-Catalyzed Enantioselective Carboiodination of Olefin-Teth-
ered Aryl Iodides. J. Am. Chem. Soc. 2019, 141, 8110. (b) Lee, Y. H.; Mo-
randi, B. Palladium-Catalyzed Intermolecular Aryliodination of Internal
Alkynes. Angew. Chem. Int. Ed. 2019, 58, 6444. (c) Sun, Y.-L.; Wang, X.-
B.; Sun, F.-N.; Cao, J.; Xu, Z.; Xu, L.-W. Enantioselective Cross-Exchange
between C-I and C-C Sigma-Bonds. Angew. Chem. Int. Ed. 2019, 58, 6747.
(d) Petrone, D. A.; Yoon, H.; Weinstabl, H.; Lautens, M. Additive Effects
in the Palladium-Catalyzed Carboiodination of Chiral N-Allyl Carbox-
amides. Angew. Chem. Int. Ed. 2014, 53, 7908. (e) Chen, C.; Hu, J.; Su, J.;
Tong, X. Synthesis of Substituted γ-Lactam via Pd(0)-Catalyzed Cycliza-
tion of Alkene-Tethered Carbamoyl Chloride. Tetrahedron Lett. 2014, 55,
AUTHOR INFORMATION
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*E-mail: glorius@uni-muenster.de
Notes
The authors declare no competing financial interests.
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229. (f) Petrone, D. A.; Lishcka, M.; Lautens, M. Harnessing Reversible
Oxidative Addition: Application of Diiodinated Aromatic Compounds in
the Carboiodination Process. Angew. Chem. Int. Ed. 2013, 52, 10635. (g)
Jia, X.; Petrone, D. A.; Lautens, M. A Conjunctive Carboiodination: in-
denes by a Double Carbopalladation-Reductive Elimination Domino Pro-
cess. Angew. Chem. Int. Ed. 2012, 51, 9870. (h) Petrone, D. A.; Malik, H.
A.; Clemenceau, A.; Lautens, M. Functionalized Chromans and Isochro-
mans via a Diastereoselective Pd (0)-Catalyzed Carboiodination. Org. Lett.
2012, 14, 4806. (i) Newman, S. G.; Lautens, M. Palladium-Catalyzed Car-
boiodination of Alkenes: Carbon-Carbon Bond Formation with Retention
of Reactive Functionality. J. Am. Chem. Soc. 2011, 133, 1778. (j) Liu, H.;
Li, C.; Qiu, D.; Tong, X. Palladium-Catalyzed Cycloisomerizations of (Z)-
1-Iodo-1,6-dienes: Iodine Atom Transfer and Mechanistic Insight to Alkyl
Iodide Reductive Elimination. J. Am. Chem. Soc. 2011, 133, 6187. (k) New-
man, S. G.; Howell, J. K.; Nicolaus, N.; Lautens, M. Palladium-catalyzed
Carbohalogenation: Bromide to Iodide Exchange and Domino Processes. J.
Am. Chem. Soc. 2011, 133, 14916. (l) Liu, H.; Chen, C.; Wang, L.; Tong.
X. Pd (0)-Catalyzed Iodoalkynation of Norbornene Scaffolds: The Remark-
able Solvent Effect on Reaction Pathway. Org. Lett. 2011, 19, 5072.
ACKNOWLEDGMENT
We thank the University of Toronto, the Natural Science and Engi-
neering Research Council (NSERC), Alphora Research Inc. and
Kennarshore Inc. for financial support. A.D.M. thanks NSERC for
an NSERC Vanier fellowship. M.W. acknowledges the financial
support of the Deutsche Forschungsgemeinschaft for a doctoral fel-
lowship (IRTG 2027 Münster-Toronto). B.M. and X.A.S. thank
OGS for funding. A.W. thanks the Province of Ontario (QEII) and
the Walter C. Sumner Memorial Fellowship for funding. We thank
Dr. Darcy Burns, Dr. Jack Sheng and Dr. Karl Demmans (Univer-
sity of Toronto) for their assistance with NMR experiments.
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