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Volumn 54, Issue 1, 2015, Pages 254-257

Synergistic steric effects in the development of a palladium-catalyzed alkyne carbohalogenation: Stereodivergent synthesis of vinyl halides

Author keywords

Carbohalogenation; Cyclization; Palladium; Reversible oxidative addition

Indexed keywords

CATALYSIS; CHLORINE COMPOUNDS; CYCLIZATION; HYDROCARBONS; ISOMERIZATION; ORGANOMETALLICS; PALLADIUM; STEREOCHEMISTRY;

EID: 84920278174     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409248     Document Type: Article
Times cited : (111)

References (40)
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    • The intermolecular carbohalogenation of alkynes using alkynyl bromides has been reported, but the authors propose the formation of a PdIV species in the catalytic cycle
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    • For substrate 1b, the isomeric products were separated by column chromatography and analyzed by 1D NOE experiments (see the Supporting Information). The cis/trans-addition ratios for all other substrates were assigned based on analogous chemical shifts in the crude 1H NMR spectra
    • 1H NMR spectra.
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    • The cis/ trans nomenclature for cyclized products 2 reflects the apparent nature of the carbopalladation step. In all cases (except for 2u), the olefin geometries of cis-2 and trans-2 are E and Z, respectively
    • The cis/ trans nomenclature for cyclized products 2 reflects the apparent nature of the carbopalladation step. In all cases (except for 2u), the olefin geometries of cis-2 and trans-2 are E and Z, respectively.
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    • Refer to the Supporting Information for further experimental details
    • Refer to the Supporting Information for further experimental details.
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    • At catalyst loadings of 7.5 mol%[Pd], a lower selectivity for cis-2e was observed (88:12 cis/trans) compared to 5.0 mol% [Pd] loading (see SI for details)
    • At catalyst loadings of 7.5 mol%[Pd], a lower selectivity for cis-2e was observed (88:12 cis/trans) compared to 5.0 mol% [Pd] loading (see SI for details).
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    • CCDC 1024942 (cis-2c), 1024943 (cis-2p), and 1024944 (trans-2p) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC 1024942 (cis-2c), 1024943 (cis-2p), and 1024944 (trans-2p) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac. uk/data-request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.