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Volumn , Issue 12, 2004, Pages 2006-2014

Rhodium-catalyzed heck-type coupling of boronic acids with activated alkenes in an aqueous emulsion

Author keywords

Alkylations; Boron; Heck reaction; Olefination; Rhodium

Indexed keywords

BORONIC ACIDS; INTERMOLECULAR COUPLING;

EID: 4444286989     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829161     Document Type: Article
Times cited : (45)

References (49)
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    • Some recent examples with boron-based reagents: (a) Chapman, C. J.; Frost, C. G. Adv. Synth. Catal. 2003, 345. (b) Yamamoto, Y.; Fujita, M.; Miyaura, N. Synlett 2002, 767. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 68, 8944. (d) Hayashi, T.; Senda, T.; Ogaswara, M. J. Am. Chem. Soc. 2000, 122, 10716. (e) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. (f) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
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    • Some recent examples with boron-based reagents: (a) Chapman, C. J.; Frost, C. G. Adv. Synth. Catal. 2003, 345. (b) Yamamoto, Y.; Fujita, M.; Miyaura, N. Synlett 2002, 767. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 68, 8944. (d) Hayashi, T.; Senda, T.; Ogaswara, M. J. Am. Chem. Soc. 2000, 122, 10716. (e) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. (f) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
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    • note
    • Boronic acids and boronate esters readily undergo transmetalation with this catalyst system; there is no noticeable difference in reactivity.
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    • 3 group has a conformational free energy (-ΔG°) of 2.4-2.5 kcal/mol, similar to an isopropyl group (2.1 kcal/mol). The value for methyl is 1.8 kcal/mol. See: (a) Nagai, T.; Nishioka, G.; Koyama, M.; Ando, A.; Miki, T.; Kumadaki, I. Chem. Pharm. Bull. 1992, 40, 593. (b) Della, E. W. J. Am. Chem. Soc. 1967, 89, 5221.
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    • 3 group has a conformational free energy (-ΔG°) of 2.4-2.5 kcal/mol, similar to an isopropyl group (2.1 kcal/mol). The value for methyl is 1.8 kcal/mol. See: (a) Nagai, T.; Nishioka, G.; Koyama, M.; Ando, A.; Miki, T.; Kumadaki, I. Chem. Pharm. Bull. 1992, 40, 593. (b) Della, E. W. J. Am. Chem. Soc. 1967, 89, 5221.
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    • note
    • 11b


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.