Synthesis of macrocycles via cobalt-mediated [2 + 2 + 2] cycloadditions

Journal of the American Chemical Society

Volumn 127, Issue 10, 2005, Pages 3473-3485

  Boñaga, Llorente V R ^a   Zhang, Han Cheng ^a   Moretto, Alessandro F ^a   Ye, Hong ^a   Gauthier, Diane A ^a   Li, Jian ^a   Leo, Gregory C ^a   Maryanoff, Bruce E ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT; IRRADIATION; REACTION KINETICS; SYRINGES; THERMAL EFFECTS; TOLUENE;

CYCLOTRIMERIZATION; ISOCYANATES; MACROCYCLES; PYRIDINE;

SYNTHESIS (CHEMICAL);

2 PHENYLETHYLISOCYANATE; COBALT; CYANAMIDE; ISOCYANATE; ISOCYANIC ACID DERIVATIVE; MACROCYCLIC COMPOUND; NITRILE; PARACYCLOPHANE DERIVATIVE; PYRIDINE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; IRRADIATION; ISOMER; SYNTHESIS; SYRINGE; TEMPERATURE;

EID: 14944380049     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045001w     Document Type: Article

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52. Intramolecular alkyne trimerizations, with the three alkyne groups in the substrate molecule, have afforded macrocyclic products with reasonable yields. (a) Lofthagen, M.; Chadha, R.; Siegel, J. S. J. Am. Chem. Soc. 1991, 113, 8785-8790. (b) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784-7785. (c) For related examples, see: Granier, T.; Cardenas, D. J.; Echavarren, A. M. Tetrahedron Lett. 2000, 41, 6775-6779. Hansen, J.; Blake, A. J.; Li, W.-S.; Mascal, M. J. Chem. Soc., Perkin Trans. 1 1998, 3371-3376. Damrauer, R.; Hankin, J. A.; Haltiwanger, R. C. Organometallics 1991, 10, 3962-3964. Mascal, M.; Hansen, J.; Blake, A. J.; Li, W.-S. Chem. Commun. 1998, 355-356. Hubert, A. J.; Hubert, M. Tetrahedron Lett. 1966, 5779-5782. Hubert, A. J. J. Chem. Soc. (C) 1967, 6-14, 1984-1985.
53. Intramolecular alkyne trimerizations, with the three alkyne groups in the substrate molecule, have afforded macrocyclic products with reasonable yields. (a) Lofthagen, M.; Chadha, R.; Siegel, J. S. J. Am. Chem. Soc. 1991, 113, 8785-8790. (b) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784-7785. (c) For related examples, see: Granier, T.; Cardenas, D. J.; Echavarren, A. M. Tetrahedron Lett. 2000, 41, 6775-6779. Hansen, J.; Blake, A. J.; Li, W.-S.; Mascal, M. J. Chem. Soc., Perkin Trans. 1 1998, 3371-3376. Damrauer, R.; Hankin, J. A.; Haltiwanger, R. C. Organometallics 1991, 10, 3962-3964. Mascal, M.; Hansen, J.; Blake, A. J.; Li, W.-S. Chem. Commun. 1998, 355-356. Hubert, A. J.; Hubert, M. Tetrahedron Lett. 1966, 5779-5782. Hubert, A. J. J. Chem. Soc. (C) 1967, 6-14, 1984-1985.
54. Intramolecular alkyne trimerizations, with the three alkyne groups in the substrate molecule, have afforded macrocyclic products with reasonable yields. (a) Lofthagen, M.; Chadha, R.; Siegel, J. S. J. Am. Chem. Soc. 1991, 113, 8785-8790. (b) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784-7785. (c) For related examples, see: Granier, T.; Cardenas, D. J.; Echavarren, A. M. Tetrahedron Lett. 2000, 41, 6775-6779. Hansen, J.; Blake, A. J.; Li, W.-S.; Mascal, M. J. Chem. Soc., Perkin Trans. 1 1998, 3371-3376. Damrauer, R.; Hankin, J. A.; Haltiwanger, R. C. Organometallics 1991, 10, 3962-3964. Mascal, M.; Hansen, J.; Blake, A. J.; Li, W.-S. Chem. Commun. 1998, 355-356. Hubert, A. J.; Hubert, M. Tetrahedron Lett. 1966, 5779-5782. Hubert, A. J. J. Chem. Soc. (C) 1967, 6-14, 1984-1985.
55. Intramolecular alkyne trimerizations, with the three alkyne groups in the substrate molecule, have afforded macrocyclic products with reasonable yields. (a) Lofthagen, M.; Chadha, R.; Siegel, J. S. J. Am. Chem. Soc. 1991, 113, 8785-8790. (b) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784-7785. (c) For related examples, see: Granier, T.; Cardenas, D. J.; Echavarren, A. M. Tetrahedron Lett. 2000, 41, 6775-6779. Hansen, J.; Blake, A. J.; Li, W.-S.; Mascal, M. J. Chem. Soc., Perkin Trans. 1 1998, 3371-3376. Damrauer, R.; Hankin, J. A.; Haltiwanger, R. C. Organometallics 1991, 10, 3962-3964. Mascal, M.; Hansen, J.; Blake, A. J.; Li, W.-S. Chem. Commun. 1998, 355-356. Hubert, A. J.; Hubert, M. Tetrahedron Lett. 1966, 5779-5782. Hubert, A. J. J. Chem. Soc. (C) 1967, 6-14, 1984-1985.
56. Intramolecular alkyne trimerizations, with the three alkyne groups in the substrate molecule, have afforded macrocyclic products with reasonable yields. (a) Lofthagen, M.; Chadha, R.; Siegel, J. S. J. Am. Chem. Soc. 1991, 113, 8785-8790. (b) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784-7785. (c) For related examples, see: Granier, T.; Cardenas, D. J.; Echavarren, A. M. Tetrahedron Lett. 2000, 41, 6775-6779. Hansen, J.; Blake, A. J.; Li, W.-S.; Mascal, M. J. Chem. Soc., Perkin Trans. 1 1998, 3371-3376. Damrauer, R.; Hankin, J. A.; Haltiwanger, R. C. Organometallics 1991, 10, 3962-3964. Mascal, M.; Hansen, J.; Blake, A. J.; Li, W.-S. Chem. Commun. 1998, 355-356. Hubert, A. J.; Hubert, M. Tetrahedron Lett. 1966, 5779-5782. Hubert, A. J. J. Chem. Soc. (C) 1967, 6-14, 1984-1985.
57. Intramolecular alkyne trimerizations, with the three alkyne groups in the substrate molecule, have afforded macrocyclic products with reasonable yields. (a) Lofthagen, M.; Chadha, R.; Siegel, J. S. J. Am. Chem. Soc. 1991, 113, 8785-8790. (b) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784-7785. (c) For related examples, see: Granier, T.; Cardenas, D. J.; Echavarren, A. M. Tetrahedron Lett. 2000, 41, 6775-6779. Hansen, J.; Blake, A. J.; Li, W.-S.; Mascal, M. J. Chem. Soc., Perkin Trans. 1 1998, 3371-3376. Damrauer, R.; Hankin, J. A.; Haltiwanger, R. C. Organometallics 1991, 10, 3962-3964. Mascal, M.; Hansen, J.; Blake, A. J.; Li, W.-S. Chem. Commun. 1998, 355-356. Hubert, A. J.; Hubert, M. Tetrahedron Lett. 1966, 5779-5782. Hubert, A. J. J. Chem. Soc. (C) 1967, 6-14, 1984-1985.
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76. 21f
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86. 15 An atmosphere of CO has been shown to regenerate the active cobalt catalyst in the Pauson-Khand reaction, see: (a) Krafft, M. E.; Boñaga, L. V. R.; Hirosawa, C. J. Org. Chem. 2001, 66, 3004-3020 and references therein. (b) Park, K. H.; Jung, I. G.; Chung, Y. K. Org. Lett. 2004, 6, 1183-1186.
87. 15 An atmosphere of CO has been shown to regenerate the active cobalt catalyst in the Pauson-Khand reaction, see: (a) Krafft, M. E.; Boñaga, L. V. R.; Hirosawa, C. J. Org. Chem. 2001, 66, 3004-3020 and references therein. (b) Park, K. H.; Jung, I. G.; Chung, Y. K. Org. Lett. 2004, 6, 1183-1186.
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89. 21a
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91. 7g
92. 2, 0.005 M in DME, reflux, ca. 18 h) to obtain low yields of benzannulated products iia (25%) or iib (10%).
93. For a preliminary report, see: Boñaga, L. V. R.; Zhang, H.-C.; Maryanoff, B. E. Chem. Commun. 2004, 2394-2395.
94. (a) Bönnemann, H.; Brijoux, W. Adv. Heterocycl. Chem. 1990, 48, 177-222.
95. (b) Bönnemann, H.; Brijoux, W. Aspects Homogen. Catal. 1984, 5, 75-196.
96. (c) Bönnemann, H.; Brijoux, W.; Brinkmann, R.; Meurers, W. Helv. Chim. Acta 1984, 67, 1616-1624.
97. (a) Heller, B.; Sundermann, B.; Buschmann, H.; Drexler, H.-J.; You, J.; Holzgrabe, U.; Heller, E.; Oehme, G. J. Org. Chem. 2002, 67, 4414-4422. Heller, B.; Reihsig, J.; Schulz, W.; Oehme, G. Appl. Organomet. Chem. 1993, 7, 641-646.
98. (a) Heller, B.; Sundermann, B.; Buschmann, H.; Drexler, H.-J.; You, J.; Holzgrabe, U.; Heller, E.; Oehme, G. J. Org. Chem. 2002, 67, 4414-4422. Heller, B.; Reihsig, J.; Schulz, W.; Oehme, G. Appl. Organomet. Chem. 1993, 7, 641-646.
99. (b) cod = 1.5-cyclooctadiene.
100. Vollhardt, K. P. C.; Naiman, A. U.S. Patent 4,328,343, 1982; Chem. Abstr. 1978, 90, 186806.
101. A survey of cyanamide reactivity with diynes of varying tethered lengths in given in ref 36.
102. Aminopyridines, which are important as pharmaceutical agents, ligands in inorganic and organometallic chemistry, and fluorescent dyes, are typically prepared by the substitution of halogenated pyridines (Thomas, S.; Roberts, S.; Pasumansky, L.; Gamsey, S.; Singaram, B. Org. Lett. 2003, 5, 3867-3870 and references therein).
103. For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
104. For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
105. For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
106. For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
107. For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
108. For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
109. For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
110. For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
111. For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
112. For a preliminary communication, see: Boñaga, L. V. R.; Zhang, H.-C.; Gauthier, D. A.; Reddy, I.; Maryanoff, B. E. Org. Lett. 2003, 5, 4537-4540.
113. The larger amount of the Co(I) catalyst was used to achieve complete reactions. DME was found to be a better solvent than 1,4-dioxane.
114. 42a For example:
115. (a) Yamamoto, Y.; Takagishi, H.; Itoh, K. Org. Lett. 2001, 13, 2117-2119.
116. 42a,b
117. cod = 1,5-cyclooctadiene; Cp* = pentamethylcyclopentadienide.
118. (a) Ulrich, H. Cycloaddition Reactions of Heterocummulenes; Academic Press: New York, 1967.
119. (b) The Chemistry of Cyanates and Their Thio Derivatives; Patai, S., Ed.; Wiley-Interscience: New York, 1977; Parts 1 and 2.
120. (c) Ozaki, S. Chem. Rev. 1972, 72, 457-496.
121. 3.
122. 2/tppts: (n) ref 16b.
123. 2/tppts: (n) ref 16b.
124. 2/tppts: (n) ref 16b.
125. 2/tppts: (n) ref 16b.
126. 2/tppts: (n) ref 16b.
127. 2/tppts: (n) ref 16b.
128. 2/tppts: (n) ref 16b.
129. 2/tppts: (n) ref 16b.
130. 2/tppts: (n) ref 16b.
131. 2/tppts: (n) ref 16b.
132. 2/tppts: (n) ref 16b.
133. 2/tppts: (n) ref 16b.
134. 2/tppts: (n) ref 16b.
135. 2/tppts: (n) ref 16b.
136. 15 See Supporting Information.
137. Dimethyl 2,2-di(prop-2-ynyl)malonate and maleic anhydride gave no cycloadduct under these reaction conditions; mostly unreacted diyne was observed at the end of the reaction.
138. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989.
139. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
140. Jaguar 4.2; Schrodinger, LLC: Portland, OR, 2002.
141. An issue of Chem. Rev. is devoted to computational transition-metal chemistry: (a) Chem. Rev. 2000, 100, 351-818. (b) Davidson, E. R. Chem. Rev. 2000, 100, 351-352. See also ref 19.
142. An issue of Chem. Rev. is devoted to computational transition-metal chemistry: (a) Chem. Rev. 2000, 100, 351-818. (b) Davidson, E. R. Chem. Rev. 2000, 100, 351-352. See also ref 19.
143. 18 without the use of syringe-pump addition or high-intensity light (see equation below).
144. This conversion presumably occurs via a retrocyclization, rotation, and ring-closure sequence. (a) Ville, G.; Vollhardt, K. P. C.; Winter, M. J. J. Am. Chem. Soc. 1981, 103, 5267-5269. (b) Fritch, J. R.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 9-11.
145. This conversion presumably occurs via a retrocyclization, rotation, and ring-closure sequence. (a) Ville, G.; Vollhardt, K. P. C.; Winter, M. J. J. Am. Chem. Soc. 1981, 103, 5267-5269. (b) Fritch, J. R.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 9-11.
146. See the Supporting Information for general experimental methods.