Heck - Suzuki - Miyaura domino reactions involving ynamides. An efficient access to 3-(arylmethylene)isoindolinones

Organic Letters

Volumn 6, Issue 15, 2004, Pages 2511-2514

  Couty, Sylvain ^a   Liégault, Benoît ^a   Meyer, Christophe ^a   Cossy, Janine ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BORONIC ACID DERIVATIVE; ISOINDOLE DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; HECK REACTION; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS;

EID: 4043137475     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049302m     Document Type: Article

References (50)

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3. Dihydroanalogues (3-alkylisoindolin-1-ones) also constitute an important class of biologically active products; see: Chen, M.-D.; Zhou, X.; He, M.-Z.; Ruan, Y.-P.; Huang, P.-Q. Tetrahedron 2004, 60, 1651-1657 and references therein.
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5. For some examples, see: (a) Pigeon, P.; Decroix, B. Tetrahedron Lett. 1996, 37, 7707-7710. (b) Ha, D.-C.; Yuun, C.-S.; Yu, E. Tetrahedron Lett. 1996, 37, 2577-2580. (c) Kato, Y.; Takemoto, M.; Achiwa, K. Chem. Pharm. Bull. 1993, 41, 2003-2006. (d) Kato, Y.; Ebiike, H.; Achiwa, K.; Ashizawa, N.; Kurihara, T.; Kobayashi, F. Chem. Pharm. Bull. 1990, 38, 2060-2062. (e) Islam, A. M.; El-Sharief, A. M. S.; Bedair, A. H.; Hammad, N. E. Egypt. J. Chem. 1983, 25, 251-261. (f) Islam, A. M.; El-Sharief, A. M. S.; El-Maghraby, A. A.; Bedear, A. H. Indian J. Chem., Sect. B 1978, 16, 301-304. (g) Marsili, A.; Scartoni, V. Gazz. Chim. Ital. 1972, 102, 806-817. (h) Marsili, A.; Scartoni, V. Tetrahedron Lett. 1968, 2511-2516.
6. For some examples, see: (a) Pigeon, P.; Decroix, B. Tetrahedron Lett. 1996, 37, 7707-7710. (b) Ha, D.-C.; Yuun, C.-S.; Yu, E. Tetrahedron Lett. 1996, 37, 2577-2580. (c) Kato, Y.; Takemoto, M.; Achiwa, K. Chem. Pharm. Bull. 1993, 41, 2003-2006. (d) Kato, Y.; Ebiike, H.; Achiwa, K.; Ashizawa, N.; Kurihara, T.; Kobayashi, F. Chem. Pharm. Bull. 1990, 38, 2060-2062. (e) Islam, A. M.; El-Sharief, A. M. S.; Bedair, A. H.; Hammad, N. E. Egypt. J. Chem. 1983, 25, 251-261. (f) Islam, A. M.; El-Sharief, A. M. S.; El-Maghraby, A. A.; Bedear, A. H. Indian J. Chem., Sect. B 1978, 16, 301-304. (g) Marsili, A.; Scartoni, V. Gazz. Chim. Ital. 1972, 102, 806-817. (h) Marsili, A.; Scartoni, V. Tetrahedron Lett. 1968, 2511-2516.
7. For some examples, see: (a) Pigeon, P.; Decroix, B. Tetrahedron Lett. 1996, 37, 7707-7710. (b) Ha, D.-C.; Yuun, C.-S.; Yu, E. Tetrahedron Lett. 1996, 37, 2577-2580. (c) Kato, Y.; Takemoto, M.; Achiwa, K. Chem. Pharm. Bull. 1993, 41, 2003-2006. (d) Kato, Y.; Ebiike, H.; Achiwa, K.; Ashizawa, N.; Kurihara, T.; Kobayashi, F. Chem. Pharm. Bull. 1990, 38, 2060-2062. (e) Islam, A. M.; El-Sharief, A. M. S.; Bedair, A. H.; Hammad, N. E. Egypt. J. Chem. 1983, 25, 251-261. (f) Islam, A. M.; El-Sharief, A. M. S.; El-Maghraby, A. A.; Bedear, A. H. Indian J. Chem., Sect. B 1978, 16, 301-304. (g) Marsili, A.; Scartoni, V. Gazz. Chim. Ital. 1972, 102, 806-817. (h) Marsili, A.; Scartoni, V. Tetrahedron Lett. 1968, 2511-2516.
8. For some examples, see: (a) Pigeon, P.; Decroix, B. Tetrahedron Lett. 1996, 37, 7707-7710. (b) Ha, D.-C.; Yuun, C.-S.; Yu, E. Tetrahedron Lett. 1996, 37, 2577-2580. (c) Kato, Y.; Takemoto, M.; Achiwa, K. Chem. Pharm. Bull. 1993, 41, 2003-2006. (d) Kato, Y.; Ebiike, H.; Achiwa, K.; Ashizawa, N.; Kurihara, T.; Kobayashi, F. Chem. Pharm. Bull. 1990, 38, 2060-2062. (e) Islam, A. M.; El-Sharief, A. M. S.; Bedair, A. H.; Hammad, N. E. Egypt. J. Chem. 1983, 25, 251-261. (f) Islam, A. M.; El-Sharief, A. M. S.; El-Maghraby, A. A.; Bedear, A. H. Indian J. Chem., Sect. B 1978, 16, 301-304. (g) Marsili, A.; Scartoni, V. Gazz. Chim. Ital. 1972, 102, 806-817. (h) Marsili, A.; Scartoni, V. Tetrahedron Lett. 1968, 2511-2516.
9. For some examples, see: (a) Pigeon, P.; Decroix, B. Tetrahedron Lett. 1996, 37, 7707-7710. (b) Ha, D.-C.; Yuun, C.-S.; Yu, E. Tetrahedron Lett. 1996, 37, 2577-2580. (c) Kato, Y.; Takemoto, M.; Achiwa, K. Chem. Pharm. Bull. 1993, 41, 2003-2006. (d) Kato, Y.; Ebiike, H.; Achiwa, K.; Ashizawa, N.; Kurihara, T.; Kobayashi, F. Chem. Pharm. Bull. 1990, 38, 2060-2062. (e) Islam, A. M.; El-Sharief, A. M. S.; Bedair, A. H.; Hammad, N. E. Egypt. J. Chem. 1983, 25, 251-261. (f) Islam, A. M.; El-Sharief, A. M. S.; El-Maghraby, A. A.; Bedear, A. H. Indian J. Chem., Sect. B 1978, 16, 301-304. (g) Marsili, A.; Scartoni, V. Gazz. Chim. Ital. 1972, 102, 806-817. (h) Marsili, A.; Scartoni, V. Tetrahedron Lett. 1968, 2511-2516.
10. For some examples, see: (a) Pigeon, P.; Decroix, B. Tetrahedron Lett. 1996, 37, 7707-7710. (b) Ha, D.-C.; Yuun, C.-S.; Yu, E. Tetrahedron Lett. 1996, 37, 2577-2580. (c) Kato, Y.; Takemoto, M.; Achiwa, K. Chem. Pharm. Bull. 1993, 41, 2003-2006. (d) Kato, Y.; Ebiike, H.; Achiwa, K.; Ashizawa, N.; Kurihara, T.; Kobayashi, F. Chem. Pharm. Bull. 1990, 38, 2060-2062. (e) Islam, A. M.; El-Sharief, A. M. S.; Bedair, A. H.; Hammad, N. E. Egypt. J. Chem. 1983, 25, 251-261. (f) Islam, A. M.; El-Sharief, A. M. S.; El-Maghraby, A. A.; Bedear, A. H. Indian J. Chem., Sect. B 1978, 16, 301-304. (g) Marsili, A.; Scartoni, V. Gazz. Chim. Ital. 1972, 102, 806-817. (h) Marsili, A.; Scartoni, V. Tetrahedron Lett. 1968, 2511-2516.
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41. For related Heck-cross-coupling domino reactions with alkynes, see: (a) Min, S.-H.; Pang, S.-J.; Cho, C.-G. Tetrahedron Lett. 2003, 44, 4439-4442. (b) Oh, C. H.; Lim, Y. M. Tetrahedron Lett. 2003, 44, 267-270. (c) Wang, R.-T.; Chou, F.-L.; Luo, F.-T. J. Org. Chem. 1990, 55, 4846-4849. (d) Grigg, R. J. Heterocycl. Chem. 1994, 31, 631-639 and references therein. (e) Negishi, E.-I.; Noda, Y.; Lamaty, F.; Vawter, E. J. Tetrahedron Lett. 1990, 31, 4393-4396. (f) Grigg, R.; Santhakumar, V.; Sridharan, V.; Stevenson, P.; Teasdale, A.; Thornton-Pett, M.; Worakun, T. Tetrahedron 1991, 47, 9703-9720. (g) Burns, B.; Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron Lett. 1989, 30, 1135-1138.
42. For related Heck-cross-coupling domino reactions with alkynes, see: (a) Min, S.-H.; Pang, S.-J.; Cho, C.-G. Tetrahedron Lett. 2003, 44, 4439-4442. (b) Oh, C. H.; Lim, Y. M. Tetrahedron Lett. 2003, 44, 267-270. (c) Wang, R.-T.; Chou, F.-L.; Luo, F.-T. J. Org. Chem. 1990, 55, 4846-4849. (d) Grigg, R. J. Heterocycl. Chem. 1994, 31, 631-639 and references therein. (e) Negishi, E.-I.; Noda, Y.; Lamaty, F.; Vawter, E. J. Tetrahedron Lett. 1990, 31, 4393-4396. (f) Grigg, R.; Santhakumar, V.; Sridharan, V.; Stevenson, P.; Teasdale, A.; Thornton-Pett, M.; Worakun, T. Tetrahedron 1991, 47, 9703-9720. (g) Burns, B.; Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron Lett. 1989, 30, 1135-1138.
43. For related Heck-cross-coupling domino reactions with alkynes, see: (a) Min, S.-H.; Pang, S.-J.; Cho, C.-G. Tetrahedron Lett. 2003, 44, 4439-4442. (b) Oh, C. H.; Lim, Y. M. Tetrahedron Lett. 2003, 44, 267-270. (c) Wang, R.-T.; Chou, F.-L.; Luo, F.-T. J. Org. Chem. 1990, 55, 4846-4849. (d) Grigg, R. J. Heterocycl. Chem. 1994, 31, 631-639 and references therein. (e) Negishi, E.-I.; Noda, Y.; Lamaty, F.; Vawter, E. J. Tetrahedron Lett. 1990, 31, 4393-4396. (f) Grigg, R.; Santhakumar, V.; Sridharan, V.; Stevenson, P.; Teasdale, A.; Thornton-Pett, M.; Worakun, T. Tetrahedron 1991, 47, 9703-9720. (g) Burns, B.; Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron Lett. 1989, 30, 1135-1138.
44. For related Heck-cross-coupling domino reactions with alkynes, see: (a) Min, S.-H.; Pang, S.-J.; Cho, C.-G. Tetrahedron Lett. 2003, 44, 4439-4442. (b) Oh, C. H.; Lim, Y. M. Tetrahedron Lett. 2003, 44, 267-270. (c) Wang, R.-T.; Chou, F.-L.; Luo, F.-T. J. Org. Chem. 1990, 55, 4846-4849. (d) Grigg, R. J. Heterocycl. Chem. 1994, 31, 631-639 and references therein. (e) Negishi, E.-I.; Noda, Y.; Lamaty, F.; Vawter, E. J. Tetrahedron Lett. 1990, 31, 4393-4396. (f) Grigg, R.; Santhakumar, V.; Sridharan, V.; Stevenson, P.; Teasdale, A.; Thornton-Pett, M.; Worakun, T. Tetrahedron 1991, 47, 9703-9720. (g) Burns, B.; Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron Lett. 1989, 30, 1135-1138.
45. For related Heck-cross-coupling domino reactions with alkynes, see: (a) Min, S.-H.; Pang, S.-J.; Cho, C.-G. Tetrahedron Lett. 2003, 44, 4439-4442. (b) Oh, C. H.; Lim, Y. M. Tetrahedron Lett. 2003, 44, 267-270. (c) Wang, R.-T.; Chou, F.-L.; Luo, F.-T. J. Org. Chem. 1990, 55, 4846-4849. (d) Grigg, R. J. Heterocycl. Chem. 1994, 31, 631-639 and references therein. (e) Negishi, E.-I.; Noda, Y.; Lamaty, F.; Vawter, E. J. Tetrahedron Lett. 1990, 31, 4393-4396. (f) Grigg, R.; Santhakumar, V.; Sridharan, V.; Stevenson, P.; Teasdale, A.; Thornton-Pett, M.; Worakun, T. Tetrahedron 1991, 47, 9703-9720. (g) Burns, B.; Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron Lett. 1989, 30, 1135-1138.
46. For related Heck-cross-coupling domino reactions with alkynes, see: (a) Min, S.-H.; Pang, S.-J.; Cho, C.-G. Tetrahedron Lett. 2003, 44, 4439-4442. (b) Oh, C. H.; Lim, Y. M. Tetrahedron Lett. 2003, 44, 267-270. (c) Wang, R.-T.; Chou, F.-L.; Luo, F.-T. J. Org. Chem. 1990, 55, 4846-4849. (d) Grigg, R. J. Heterocycl. Chem. 1994, 31, 631-639 and references therein. (e) Negishi, E.-I.; Noda, Y.; Lamaty, F.; Vawter, E. J. Tetrahedron Lett. 1990, 31, 4393-4396. (f) Grigg, R.; Santhakumar, V.; Sridharan, V.; Stevenson, P.; Teasdale, A.; Thornton-Pett, M.; Worakun, T. Tetrahedron 1991, 47, 9703-9720. (g) Burns, B.; Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron Lett. 1989, 30, 1135-1138.
47. For related Heck-cross-coupling domino reactions with alkynes, see: (a) Min, S.-H.; Pang, S.-J.; Cho, C.-G. Tetrahedron Lett. 2003, 44, 4439-4442. (b) Oh, C. H.; Lim, Y. M. Tetrahedron Lett. 2003, 44, 267-270. (c) Wang, R.-T.; Chou, F.-L.; Luo, F.-T. J. Org. Chem. 1990, 55, 4846-4849. (d) Grigg, R. J. Heterocycl. Chem. 1994, 31, 631-639 and references therein. (e) Negishi, E.-I.; Noda, Y.; Lamaty, F.; Vawter, E. J. Tetrahedron Lett. 1990, 31, 4393-4396. (f) Grigg, R.; Santhakumar, V.; Sridharan, V.; Stevenson, P.; Teasdale, A.; Thornton-Pett, M.; Worakun, T. Tetrahedron 1991, 47, 9703-9720. (g) Burns, B.; Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron Lett. 1989, 30, 1135-1138.
48. Apparently, the Heck - Suzuki - Miyaura domino reactions afforded the 3-(arylmethylene)isoindolin-1-ones described herein as single geometric isomers. However, we cannot rule out that for some substrates of this class, depending on the aryl group and the nitrogen substituent, equilibration may further occur especially by acid-catalyzed, hydration - dehydration, or photochemical processes.
49. Authentic samples of the (Z)-isomers of compounds 10 and 12 were prepared from amides 2b and 2d, respectively, by Sonogashira coupling with phenylacetylene and subsequent base-induced ring-closure (EtONa/ EtOH). The stereochemical outcome of this literature procedure has been unambiguously established (see ref 1a).
50. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.