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23044480768
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note
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With enantiopure L1, the complex 1 was clearly identified by NMR spectroscopy. The acetato-bridged structure was supported by the ESI mass spectrum of the palladium complex 1 (see Supporting Information).
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29
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3843073059
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2 symmetry and retention of configuration at phosphorus (see Supporting Information). During the course of our work, Leung and co-workers reported chiral bisphosphinite metalloligands derived from a P-chiral secondary phosphine oxide: E. Y. Y. Chan, Q. F. Zhang, Y.-K. Sau, S. M. F. Lo, H. H. Y. Sung, I. D. Williams, R. K. Haynes, W-H. Leung, Inorg. Chem. 2004, 43, 4921-4926.
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Haynes, R.K.7
Leung, W.-H.8
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30
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23044515384
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note
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Cycloadduct 3a was also contaminated with 5% of an unidentified byproduct.
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32
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0032742849
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23044452751
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(Ed.: S-I. Murahashi), Wiley-VCH, Weinheim, chap. 4
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Yamamoto, Y.1
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39
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23044498434
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note
-
3 (dba = dibenzylideneacetone) did not promote the reaction at all.
-
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-
-
40
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23044483135
-
-
note
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3CN (6% yield).
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-
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41
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23044505145
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note
-
The catalytic system was stable under the experimental conditions described and could be recovered after the reaction by column chromatography.
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42
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23044499764
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note
-
A difference in reactivity was observed by using trimethylsilylacetylene in place of propargylsilane 3c: Only an adduct of hydroalkynylation was obtained as a single diastereomer in 68% yield.
-
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43
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23044472298
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Wiley, Chichester, chap. 6
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0-catalyzed reactions of various propargylic compounds proceed by the formation of either σ-allenyl or σ-prop-2-ynylpalladium species; see: J. Tsuji, Palladium Reagents and Catalysts: New Perspectives for the 21st Century, Wiley, Chichester, 2004, chap. 6, pp. 543-563;
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Tsuji, J.1
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44
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85014698070
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Wiley, Chichester, chap. 7
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II-catalyzed reactions of alkynes, see: J. Tsuji, Palladium Reagents and Catalysts: New Perspectives for the 21st Century, Wiley, Chichester, 2004, chap. 7, pp. 565-599.
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23044460977
-
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see reference [21a]
-
2π mechanism, which is a symmetry-forbidden reaction. They have therefore been generally interpreted to occur by cleavage to a diradical followed by rapid intramolecular trapping of the diradical by the π bond (see reference [21a]).
-
-
-
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48
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23044436566
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-
see reference [36]
-
The structure and stereochemistry of compounds 4i and 6i were confirmed by X-ray analysis (see reference [36]).
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-
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49
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23044489570
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note
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The same reaction carried out with cyclopentene in place of norbornene derivatives did not work. No oligomers or self-coupling adducts of the phenylethyne 3a have been observed.
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50
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0000732541
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0031046817
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For examples of terminal alkyne-alkyne couplings catalyzed by palladium, see: B. M. Trost, M. T. Sorum, C. Chan, A. E. Harms, G. Rühter, J. Am. Chem. Soc. 1997, 119, 698-708.
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Menéndez, C.1
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58
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23044466971
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note
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2-coordinated alkyne intermediate A. The first involves a direct 1,2-hydrogen migration over the carbon triple bond. In contrast, the second mechanism occurs through a 1,3-shift of the hydride to the alkynyl ligand after oxidative addition of the C-H bond to Pd.
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59
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23044505408
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note
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sp2-H at δ = 6.55 ppm (see Supporting Information).
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60
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0003015381
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For recent reviews, see: a) H, Werner, Chem. Commun. 1997, 903-910;
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Werner, H.1
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63
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23044444664
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note
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2) columns using hexane/ethanol (90:10) or ethanol as eluents. For L2, the absolute configuration at phosphorus is currently unknown.
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68
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23044514908
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Wiley, New York, chap. 14-3
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This type of chirality known under the name of "geometric enantiomerism" is also called cis-trans enantiomerism. Stereochemistry of Organic Compounds (Eds.: E. L. Eliel, S. H. Wilen), Wiley, New York, 1994, chap. 14-3, pp. 1155-1156.
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Stereochemistry of Organic Compounds
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Eliel, E.L.1
Wilen, S.H.2
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69
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0001500173
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Alkylidenecyclopropanes have served as useful building blocks in organic synthesis. For recent reviews, see: a) I. Nakamura, Y. Yamamoto. Adv. Synth. Catal. 2002, 344, 111-217;
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Adv. Synth. Catal.
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Brandi, A.1
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71
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23044489183
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See Supporting Information for full synthetic details and characterization of new compounds. CCDC 265344-265346 (4i, 6i, and 5) contain 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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