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Volumn 349, Issue 11-12, 2007, Pages 2054-2060

Substituted benzocarbocycles by palladium-catalyzed cascade reactions featuring a C(sp3) - H activation step

Author keywords

Benzocarbocycles; C H activation; Cascade reactions; Heck reaction; Hydroge; Palladium

Indexed keywords


EID: 34548420074     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700099     Document Type: Article
Times cited : (39)

References (44)
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    • Recent examples of palladium-catalyzed pure domino sequences involving a C-H activation step: a) A. Kong, X. Han, X. Lu, Org. Lett. 2006, 8, 1339-1342;
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    • For a recent related example of 5-endo-trig Heck cyclization, see: P. Vital, P.-O. Norrby, D. Tanner, Synlett 2006,18, 3140-3144.
    • For a recent related example of 5-endo-trig Heck cyclization, see: P. Vital, P.-O. Norrby, D. Tanner, Synlett 2006,18, 3140-3144.
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    • JohnPhos: 2-(di-ferf-butylphosphino)biphenyl, see: A. Aranyos, D. W. Old, A. Kiyomori, J. P. Wolfe, J. P. Sadighi, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 4369-4378.
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    • On the contrary, starting from lb, the final product is formed earlier in the process and is consequently more prone to decomposition. This may partly account for the modest yields observed with this substrate when the 4-membered ring is favored.
    • On the contrary, starting from lb, the final product is formed earlier in the process and is consequently more prone to decomposition. This may partly account for the modest yields observed with this substrate when the 4-membered ring is favored.
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    • Other examples: S. Caddick, W. Kofie, Tetrahedron Lett. 2002, 43, 9347-9350.
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    • 3) - H activation/Heck cyclization 2 step process, only moderate overall yields were observed most probably due to partial decomposition of the heat-sensitive exo-methylenebenzocyclobutene moiety during the Heck steps, that lowered the efficiency of these usually high-yielding reactions and, consequently, of the overall 3-step process.
    • 3) - H activation/Heck cyclization 2 step process, only moderate overall yields were observed most probably due to partial decomposition of the heat-sensitive exo-methylenebenzocyclobutene moiety during the Heck steps, that lowered the efficiency of these usually high-yielding reactions and, consequently, of the overall 3-step process.
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    • See Supporting information for details
    • See Supporting information for details.
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    • In these cases, a larger excess of aryl bromide 4 equivs, was employed in order to reach maximum conversion before catalyst deactivation
    • In these cases, a larger excess of aryl bromide (4 equivs.) was employed in order to reach maximum conversion before catalyst deactivation.
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    • See Supporting information for a micrograph
    • See Supporting information for a micrograph.
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    • Benzocyclobutenes are useful building blocks, especially in cycloaddition reactions: G. Mehta, S. Kotha, Tetrahedron 2001, 57, 625-659;
    • Benzocyclobutenes are useful building blocks, especially in cycloaddition reactions: G. Mehta, S. Kotha, Tetrahedron 2001, 57, 625-659;


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.