Catalytic three-component coupling of alkynes, imines, and organoboron reagents

Angewandte Chemie - International Edition

Volumn 42, Issue 12, 2003, Pages 1364-1367

  Patel, Sejal J ^a   Jamison, Timothy F ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Alkynes; Allylic amines; Boronic acids; Imines; Nickel

Indexed keywords

AGENTS; BORON; CATALYSIS; ESTERS; KETONES; ORGANOMETALLICS; SOLVENTS;

ORGANOBORON REAGENTS;

AMINES;

ALKYNE; BORANE DERIVATIVE; BORONIC ACID DERIVATIVE; ESTER; HYDROXYL GROUP; IMINE; KETONE; SOLVENT;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHIRALITY; MOLECULAR DYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; STEREOCHEMISTRY;

ALKYNES; ALLYL COMPOUNDS; AMINES; BORON COMPOUNDS; CATALYSIS; IMINES; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 0037471214     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390349     Document Type: Article

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16. Reductive coupling of alkynes and imines by using early transition metal complexes: a) S. L. Buchwald, B. T. Watson, M. W. Wannamaker, J. C. Dewan, J. Am. Chem. Soc. 1989, 111, 4486; b) M. Jensen, T. Livinghouse, J. Am. Chem. Soc. 1989, 111, 4495; c) K. Takai, S. Miwatashi, Y. Kataoka, K. Utimoto, Chem. Lett. 1992, 99; d) Y. Gao, K. Harada, F. Sato, Tetrahedron Lett. 1995, 36, 5913; alkenylmetal additions to imines and related electrophiles: e) S. E. Denmark, N. Nakajima, O. J.-C. Nicaise, J. Am. Chem. Soc. 1994, 116, 8797; f) N. A. Petasis, I. A. Zavialov, J. Am. Chem. Soc. 1997, 119, 445; g) N. A. Petasis, I. A. Zavialov, J. Am. Chem. Soc. 1998, 120, 11798; h) R. A. Batey, D. B. MacKay, V. Santhakumar, J. Am. Chem. Soc. 1999, 121, 5075; i) P. Wipf, C. Kendall, C. R. J. Stephenson, J. Am. Chem. Soc. 2001, 123, 5122; j) review: M. Johannsen, K. A. Jørgensen, Chem. Rev. 1998, 98, 1689.
17. Reductive coupling of alkynes and imines by using early transition metal complexes: a) S. L. Buchwald, B. T. Watson, M. W. Wannamaker, J. C. Dewan, J. Am. Chem. Soc. 1989, 111, 4486; b) M. Jensen, T. Livinghouse, J. Am. Chem. Soc. 1989, 111, 4495; c) K. Takai, S. Miwatashi, Y. Kataoka, K. Utimoto, Chem. Lett. 1992, 99; d) Y. Gao, K. Harada, F. Sato, Tetrahedron Lett. 1995, 36, 5913; alkenylmetal additions to imines and related electrophiles: e) S. E. Denmark, N. Nakajima, O. J.-C. Nicaise, J. Am. Chem. Soc. 1994, 116, 8797; f) N. A. Petasis, I. A. Zavialov, J. Am. Chem. Soc. 1997, 119, 445; g) N. A. Petasis, I. A. Zavialov, J. Am. Chem. Soc. 1998, 120, 11798; h) R. A. Batey, D. B. MacKay, V. Santhakumar, J. Am. Chem. Soc. 1999, 121, 5075; i) P. Wipf, C. Kendall, C. R. J. Stephenson, J. Am. Chem. Soc. 2001, 123, 5122; j) review: M. Johannsen, K. A. Jørgensen, Chem. Rev. 1998, 98, 1689.
18. Reductive coupling of alkynes and imines by using early transition metal complexes: a) S. L. Buchwald, B. T. Watson, M. W. Wannamaker, J. C. Dewan, J. Am. Chem. Soc. 1989, 111, 4486; b) M. Jensen, T. Livinghouse, J. Am. Chem. Soc. 1989, 111, 4495; c) K. Takai, S. Miwatashi, Y. Kataoka, K. Utimoto, Chem. Lett. 1992, 99; d) Y. Gao, K. Harada, F. Sato, Tetrahedron Lett. 1995, 36, 5913; alkenylmetal additions to imines and related electrophiles: e) S. E. Denmark, N. Nakajima, O. J.-C. Nicaise, J. Am. Chem. Soc. 1994, 116, 8797; f) N. A. Petasis, I. A. Zavialov, J. Am. Chem. Soc. 1997, 119, 445; g) N. A. Petasis, I. A. Zavialov, J. Am. Chem. Soc. 1998, 120, 11798; h) R. A. Batey, D. B. MacKay, V. Santhakumar, J. Am. Chem. Soc. 1999, 121, 5075; i) P. Wipf, C. Kendall, C. R. J. Stephenson, J. Am. Chem. Soc. 2001, 123, 5122; j) review: M. Johannsen, K. A. Jørgensen, Chem. Rev. 1998, 98, 1689.
19. Reductive coupling of alkynes and imines by using early transition metal complexes: a) S. L. Buchwald, B. T. Watson, M. W. Wannamaker, J. C. Dewan, J. Am. Chem. Soc. 1989, 111, 4486; b) M. Jensen, T. Livinghouse, J. Am. Chem. Soc. 1989, 111, 4495; c) K. Takai, S. Miwatashi, Y. Kataoka, K. Utimoto, Chem. Lett. 1992, 99; d) Y. Gao, K. Harada, F. Sato, Tetrahedron Lett. 1995, 36, 5913; alkenylmetal additions to imines and related electrophiles: e) S. E. Denmark, N. Nakajima, O. J.-C. Nicaise, J. Am. Chem. Soc. 1994, 116, 8797; f) N. A. Petasis, I. A. Zavialov, J. Am. Chem. Soc. 1997, 119, 445; g) N. A. Petasis, I. A. Zavialov, J. Am. Chem. Soc. 1998, 120, 11798; h) R. A. Batey, D. B. MacKay, V. Santhakumar, J. Am. Chem. Soc. 1999, 121, 5075; i) P. Wipf, C. Kendall, C. R. J. Stephenson, J. Am. Chem. Soc. 2001, 123, 5122; j) review: M. Johannsen, K. A. Jørgensen, Chem. Rev. 1998, 98, 1689.
20. Reductive coupling of alkynes and imines by using early transition metal complexes: a) S. L. Buchwald, B. T. Watson, M. W. Wannamaker, J. C. Dewan, J. Am. Chem. Soc. 1989, 111, 4486; b) M. Jensen, T. Livinghouse, J. Am. Chem. Soc. 1989, 111, 4495; c) K. Takai, S. Miwatashi, Y. Kataoka, K. Utimoto, Chem. Lett. 1992, 99; d) Y. Gao, K. Harada, F. Sato, Tetrahedron Lett. 1995, 36, 5913; alkenylmetal additions to imines and related electrophiles: e) S. E. Denmark, N. Nakajima, O. J.-C. Nicaise, J. Am. Chem. Soc. 1994, 116, 8797; f) N. A. Petasis, I. A. Zavialov, J. Am. Chem. Soc. 1997, 119, 445; g) N. A. Petasis, I. A. Zavialov, J. Am. Chem. Soc. 1998, 120, 11798; h) R. A. Batey, D. B. MacKay, V. Santhakumar, J. Am. Chem. Soc. 1999, 121, 5075; i) P. Wipf, C. Kendall, C. R. J. Stephenson, J. Am. Chem. Soc. 2001, 123, 5122; j) review: M. Johannsen, K. A. Jørgensen, Chem. Rev. 1998, 98, 1689.
21. Reductive coupling of alkynes and imines by using early transition metal complexes: a) S. L. Buchwald, B. T. Watson, M. W. Wannamaker, J. C. Dewan, J. Am. Chem. Soc. 1989, 111, 4486; b) M. Jensen, T. Livinghouse, J. Am. Chem. Soc. 1989, 111, 4495; c) K. Takai, S. Miwatashi, Y. Kataoka, K. Utimoto, Chem. Lett. 1992, 99; d) Y. Gao, K. Harada, F. Sato, Tetrahedron Lett. 1995, 36, 5913; alkenylmetal additions to imines and related electrophiles: e) S. E. Denmark, N. Nakajima, O. J.-C. Nicaise, J. Am. Chem. Soc. 1994, 116, 8797; f) N. A. Petasis, I. A. Zavialov, J. Am. Chem. Soc. 1997, 119, 445; g) N. A. Petasis, I. A. Zavialov, J. Am. Chem. Soc. 1998, 120, 11798; h) R. A. Batey, D. B. MacKay, V. Santhakumar, J. Am. Chem. Soc. 1999, 121, 5075; i) P. Wipf, C. Kendall, C. R. J. Stephenson, J. Am. Chem. Soc. 2001, 123, 5122; j) review: M. Johannsen, K. A. Jørgensen, Chem. Rev. 1998, 98, 1689.
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34. 3CN, or EtOAc as solvent gave mixtures of 1a and 2a in <10% yield.
35. 2Zn, polymethylhydrosiloxane (PMHS), and Et3SiH gave complex mixtures of undesired products corresponding to imine addition and/or reduction.
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38. This phenomenon probably does not result from water, as substoichiometric, stoichiometric, or excess amounts depreciate yield. EtOH and iPrOH gave significantly lower yields.
39. Reactions conducted with diphosphanes as ligands (BINAP, dppe, dppb) gave trace amounts of allylic amines.
40. With 1-phenyl-2-(trimethylsilyl)acetylene, allylic amine 1n is formed in 22% yield (regioselectivity >98:2) under the standard reaction conditions.
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