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(4) For selected references of earlier contributions in
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Kawatsura, M.; Hartwig, J. F. "Palladium-Catalyzed
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of Alkenes: Use of a Benzyl Group as a Traceless Redox-
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(10) For
a
seminal contribution for preparation of
azidoiodinane from benziodoxole and their reactivity
studies, see: a) Zhdankin, V. V.; Krasutsky, A. P.; Kuehl,
C. J.; Simonsen, A. J.; Woodward, J. K.; Mismash, B.; Bolz,
J. T. "Preparation, X-ray Crystal Structure, and Chemistry
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Am. Chem. Soc. 1996, 118, 5192. For selected reviews of
hypervalent iodine reagents prepared from benziodoxole,
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Atom-Transfer Reactions." Chem. Commun. 2011, 47, 102;
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1712; e) Hari, D. P.; Caramenti, P.; Waser, J. "Cyclic
Hypervalent Iodine Reagents: Enabling Tools for Bond
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2018, 51, 3212. See also, f) Alazet, S.; LeꢀVaillant, F.;
Nicolai, S.; Courant, T.; Waser, J. "Divergent Access to
(1,1) and (1,2)-Azidolactones from Alkenes using
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9501.
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Widenhoefer, R. A. "Intermolecular Hydroamination of
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2008, 108, 3795. For
a
selected reference of
intramolecular hydroamination in complex-molecule
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(12) Further decreased loading of 2a (0.05 equiv) leads to
incomplete conversion (entry 9); see SI for details.
(13) For stereochemistry determination of 7, see SI. The
stereochemistry of 8 was determined through X-ray
crystallographic analysis of a derivative of 8, see SI for
details.
(14) For selected references of syntheses of 1,3-
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Aubé, J. "One-Step Conversion of Aldehydes to
Oxazolines and 5,6-Dihydro-4H-1,3-oxazines Using 1,2-
and 1,3-Azido Alcohols." J. Org. Chem. 1996, 61, 2484; b)
Li, C.; Peters, A. S.; Meredith, E. L.; Allman, G. W.;
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Zhou,
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"Iridium-Catalyzed,
Intermolecular Hydroamination of Unactivated Alkenes
with Indoles." J. Am. Chem. Soc. 2014, 136, 3200. For a
selected reference of olefin hydroamination sequence
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Waser, J.; Gaspar, B.; Nambu, H.; Carreira, E. M.
"Hydrazines and Azides via the Metal-Catalyzed
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(15) Low reactivity observed in hydroazidation of allyl silanes,
allylbenzene, and allylic esters may be due to slow H-
atom transfer from HN3 to the reversibly generated,
stabilized -azido radicals, see SI for details.
(16) Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. "Organic
Azides: An Exploding Diversity of a Unique Class of
Compounds." Angew. Chem., Int. Ed. 2005, 44, 5188.
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