Ligands for Palladium-Catalyzed Cross-Couplings of Alkyl Halides: Use of an Alkyldiaminophosphane Expands the Scope of the Stille Reaction

Angewandte Chemie - International Edition

Volumn 42, Issue 41, 2003, Pages 5079-5082

  Tang, Haifeng ^a   Menzel, Karsten ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Cross coupling; Homogeneous catalysis; Palladium; Phosphane ligands; Stille reaction

Indexed keywords

PALLADIUM; PHOSPHORUS COMPOUNDS; TIN COMPOUNDS;

LIGANDS;

CATALYSIS;

ALKYL GROUP; DIAMINOPHOSPHANE DERIVATIVE; FUNCTIONAL GROUP; HALIDE; LIGAND; PALLADIUM; PHOSPHORUS DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON; ROOM TEMPERATURE; STILLE REACTION; SYNTHESIS;

CATALYSIS; HYDROCARBONS, BROMINATED; LIGANDS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; ORGANOPHOSPHORUS COMPOUNDS; PALLADIUM; TIN COMPOUNDS;

EID: 0242354878     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352668     Document Type: Article

References (45)

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32. See reference [8], including footnote [15].
33. 3 are the most effective.
34. a) Verkade has established that certain triaminophosphanes provide reactive catalysts for palladium-catalyzed Suzuki and Buchwald-Hartwig cross-couplings of aryl halides. See: S. Urgaonkar, M. Nagarajan, J. G. Verkade, Tetrahedron Lett. 2002, 43, 8921-8924; S. Urgaonkar, M. Nagarajan, J. G. Verkade, Org. Lett. 2003, 5, 815-818; S. Urgaonkar, M. Nagarajan, J. G. Verkade, J. Org. Chem. 2003, 68, 452-459;
35. a) Verkade has established that certain triaminophosphanes provide reactive catalysts for palladium-catalyzed Suzuki and Buchwald-Hartwig cross-couplings of aryl halides. See: S. Urgaonkar, M. Nagarajan, J. G. Verkade, Tetrahedron Lett. 2002, 43, 8921-8924; S. Urgaonkar, M. Nagarajan, J. G. Verkade, Org. Lett. 2003, 5, 815-818; S. Urgaonkar, M. Nagarajan, J. G. Verkade, J. Org. Chem. 2003, 68, 452-459;
36. a) Verkade has established that certain triaminophosphanes provide reactive catalysts for palladium-catalyzed Suzuki and Buchwald-Hartwig cross-couplings of aryl halides. See: S. Urgaonkar, M. Nagarajan, J. G. Verkade, Tetrahedron Lett. 2002, 43, 8921-8924; S. Urgaonkar, M. Nagarajan, J. G. Verkade, Org. Lett. 2003, 5, 815-818; S. Urgaonkar, M. Nagarajan, J. G. Verkade, J. Org. Chem. 2003, 68, 452-459;
37. b) With acyclic triaminophosphanes, we have obtained small amounts of Stille cross-coupling products.
38. 2 is ineffective.
39. 3 proceed in more modest yield. 2) Allylstannanes, alkynylstannanes, alkyl chlorides, alkyl tosylates, and certain (tertiary, secondary, and β-branched primary) alkyl bromides are not useful coupling partners, furnishing at best a poor yield of the desired product.
40. 31P NMR.
41. For a discussion and leading references, see Reference [8].
42. 2, leads to a significant loss in yield (<50%).
43. 2Me, reactions run at higher concentration lead to the precipitation of a black solid, presumably Pd).
44. 2.
45. Under these conditions, we have also efficiently coupled 1-iododecane with tributyl(vinyl)tin (93% yield by GC versus a calibrated internal standard).