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Volumn , Issue 18, 2006, Pages 2908-2913

A mixed naphthyl-phenyl phosphine ligand motif for Suzuki, Heck, and hydrodehalogenation reactions

Author keywords

Cross coupling; Dehydrohalogenation; Heck reaction; Hindered biaryls; Homogenous catalysis; Phosphorus ligand; Suzuki Miyaura

Indexed keywords

BENZENE DERIVATIVE; DICYCLOHEXYL [4 METHOXY 3 (2 METHOXYPHENYL)NAPHTH 2 YL]PHOSPHINE; DICYCLOHEXYL [4 METHOXY 3 (2 METHOXYPHENYL)NAPHTH 2 YL]PHOSPHINOXIDE; NAPHTHALENE; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33751278742     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951538     Document Type: Article
Times cited : (42)

References (43)
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    • (a) For an outstanding critical review on the Heck and Suzuki reactions focusing on the active species, which presents a detailed analysis of P-ligands, see: Phan, N. T. S.; Van Der Sluys, M.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 609.
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    • (b) For a review on hydrophilic P-based ligands, see: Shaughnessy, K. H. Eur. J. Chem. 2006, 1827.
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    • For a practical synthesis of biphenyl phosphine ligands using a Grignard-benzyne reaction, see: (a) Tomori, H.; Fox, J. M.; Buchwald, S. L. J. Org. Chem. 2000, 65, 5334.
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    • For recent work, see and references cited therein
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    • note
    • 6 solution. Crystallographic data (excluding structure factors) for the structure of 4 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-609270. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK [fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk). (diagram presented) Figure 2 X-ray crystal structure of 4. For clarity, hydrogen atoms are excluded except those involved in hydrogen bonding.
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    • For similar nucleophilic aromatic substitutions driven by coordination effects, see: (a) Meyers, A. I.; Hummelsbach, R. J. J. Am. Chem. Soc. 1985, 107, 682.
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    • note
    • 3SiH with the more economical and non-toxic polyhydromethylsiloxane (PMHS), as suggested in the above reference, was similarly effective (110 °C, 56 h) but caused problems of incomplete separation of polymeric siloxanes in column chromatography.
  • 31
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    • note
    • 2 ratio produced a very active catalyst, leading to 50% product formation in 15 min in DMF or MeOH at 40 °C (Table 1, entry 1).
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    • For previous cross-coupling of hindered benzamides which required special conditions and led to poorer yields, see: Fu, J.-m.; Sharp, M. J.; Snieckus, V. Tetrahedron Lett. 1988, 29, 5459.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 5459
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    • note
    • 6a Nap-Phos (70%).
  • 43
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    • note
    • A preliminary PM3 modeling study shows a low racemization barrier (20 kcal/mol) for Nap-Phos which precludes its use as a chiral ligand in cross coupling reactions under conditions described herein. Few chiral non-racemic atropisomeric ligand motifs are known. For discussion, see ref. 14c.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.