Copper-catalyzed coupling of imines, acid chlorides, and alkynes: A multicomponent route to propargylamides

Organic Letters

Volumn 6, Issue 7, 2004, Pages 1107-1110

  Black, Daniel A ^a   Arndtsen, Bruce A ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALKYNE; AMIDE; CARBAMIC ACID; CHLORIDE; CHLOROFORMATE; COPPER; FORMIC ACID DERIVATIVE; IMINE; PROPARGYLAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; STRUCTURE ANALYSIS;

EID: 2342468598     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036462+     Document Type: Article

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6. Classical examples of MCRs: (a) Ugi, I.; Steinbrueckner, C. Chem. Ber. 1961, 94, 2802-2814. (b) Strecker, A. Ann. Chem. 1850, 75, 27-45. (c) Mannich, C.; Kösche, W. Arch. Pharm. (Weinheim, Ger.) 1912, 250, 647-667. Hantzsch, A. Ber. Dtsch. Chem. Ges. 1890, 23, 1474-1476.
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10. Representative examples: (a) Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010-1027. (b) Montgomery, J. Acc. Chem. Res. 2000, 33, 467-473. (c) Dhawan, R., Dghaym, R. D., Arndtsen, B. A. J. Am. Chem. Soc. 2003, 125, 1474-1475. Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 7786-7787. (e) Tessier, P. E.; Penwell, A. J.; Souza, F. E. S.; Fallis, A. G. Org. Lett. 2003, 5, 2989-2992. (f) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 2000, 122, 8081-8082. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880-2881. (h) Rao, I. N.; Prabhakaran, E. N.; Das, S. K.; Iqbal, J. J. Org. Chem. 2003, 68, 4079-4082.
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13. Representative examples: (a) Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010-1027. (b) Montgomery, J. Acc. Chem. Res. 2000, 33, 467-473. (c) Dhawan, R., Dghaym, R. D., Arndtsen, B. A. J. Am. Chem. Soc. 2003, 125, 1474-1475. (d) Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 7786-7787. (e) Tessier, P. E.; Penwell, A. J.; Souza, F. E. S.; Fallis, A. G. Org. Lett. 2003, 5, 2989-2992. (f) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 2000, 122, 8081-8082. (g) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880-2881. (h) Rao, I. N.; Prabhakaran, E. N.; Das, S. K.; Iqbal, J. J. Org. Chem. 2003, 68, 4079-4082.
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54. α-Chloroamides are established to undergo rapid acid elimination to generate enamides (ref 25). Studies are currently underway to examine the potential use of more coordinating anions to inhibit this elimination relative to alkynylation.
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56. The lack of any ligand influence on the reaction rates argues against an oxidative addition-based pathway.
57. The lack of ketone products (from acetylide reaction with acid chloride) can be attributed to the fast generation of 3, which undergoes rapid coupling (rt, 15 min) coupling with 2.