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K2S2O8 oxidizes alkyl boronates to alkyl R radicals and engages in alkynylation with BI-alkyne, see Refs.[9] and [7b]. Its inability for alkenylation also suggests the formation of a BI complex similar to BI-alkyne. See Schemes S6, S15, and Table S1
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K2S2O8 oxidizes alkyl boronates to alkyl R radicals and engages in alkynylation with BI-alkyne, see Refs.[9] and [7b]. Its inability for alkenylation also suggests the formation of a BI complex similar to BI-alkyne. See Schemes S6, S15, and Table S1.
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35
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84964198821
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The reduction of BI-OCOR by photoexcited [RuII] is very slow (see Scheme S4), which implies that it is not the major reaction pathway for generating benziodoxole radicals
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The reduction of BI-OCOR by photoexcited [RuII] is very slow (see Scheme S4), which implies that it is not the major reaction pathway for generating benziodoxole radicals.
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36
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66149154557
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A radical a-addition to vinyl carboxylates was observed before. See
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77249159352
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The radical aaddition was also confirmed by a 13C-labeling experiment; see Scheme S16. A b-addition to Michael acceptors was observed in the previous iridium photocatalyst system. See Refs. [8a,b], which suggests the distinction between these two photoredox systems
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Y. Abe, T. Sawada, M. Takafuji, T. Mashimo, M. Ono, H. Ihara, Chem. Lett. 2010, 39, 174 - 175. The radical aaddition was also confirmed by a 13C-labeling experiment; see Scheme S16. A b-addition to Michael acceptors was observed in the previous iridium photocatalyst system. See Refs. [8a,b], which suggests the distinction between these two photoredox systems.
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For leading examples on benziodoxole radical, see
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For leading examples on benziodoxole radical, see:
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84964309336
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It is unclear at this point if the effective reaction of cyclic iodine(III) compared to noncyclic iodine(III) reagents is due to the reactivity of the benziodoxole vinyl carboxylic acid complex, or the benziodoxole radical, or other reasons
-
It is unclear at this point if the effective reaction of cyclic iodine(III) compared to noncyclic iodine(III) reagents is due to the reactivity of the benziodoxole vinyl carboxylic acid complex, or the benziodoxole radical, or other reasons.
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The previously reported transition-metal-catalyzed alkyl radical addition to vinyl carboxylic acids involved internal singleelectron transfer to generate carbocations; see Ref.3.
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84964280830
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The alkyl-substituted vinyl carboxylic acids gave no alkenylation product, possibly because the resulting radical was not stabilized; see Scheme S18. Similar results were observed in other alkyl Heck-type reactions as well; see Ref.19
-
The alkyl-substituted vinyl carboxylic acids gave no alkenylation product, possibly because the resulting radical was not stabilized; see Scheme S18. Similar results were observed in other alkyl Heck-type reactions as well; see Ref.19.
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59
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84893555273
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This report is mechanistically different from decarboxylative trifluoromethylation of vinyl carboxylates using Togni reagents: See Scheme S10
-
This report is mechanistically different from decarboxylative trifluoromethylation of vinyl carboxylates using Togni reagents: P. Xu, A. Abdukader, K. Hu, Y. Cheng, C. Zhu, Chem. Commun. 2014, 50, 2308 - 2310. See Scheme S10.
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Xu, P.1
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Hu, K.3
Cheng, Y.4
Zhu, C.5
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60
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84964269306
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CCDC cd214216 (9) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
-
CCDC cd214216 (9) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
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