Matches in SemOpenAlex for { <https://semopenalex.org/work/W2969601412> ?p ?o ?g. }
- W2969601412 endingPage "9044" @default.
- W2969601412 startingPage "9034" @default.
- W2969601412 abstract "The remote, diastereoselective hydroboration of 2- and 3-substituted indenes with a 2,2′:6′,2″-terpyridine cobalt alkyl precatalyst is described that maintains high regio- and stereoselectivity independent of the starting position of the alkene. Several 1,2- and 1,3-disubstituted indanyl boronate esters were obtained with exclusive (>20:1 dr) selectivity for the trans diastereomer including synthetically versatile, stereodefined diboron derivatives. Alkene isomerization by a putative cobalt hydride intermediate precedes carbon–boron bond formation, leading to the observed regioselectivity for boron incorporation at the unsubstituted C(sp3)–H benzylic site. The regio- and diastereoselectivity of the transformation were maintained independent of the starting position of the alkene, as demonstrated by hydroboration of three isomers of methyl-substituted indene. Deuterium-labeling experiments support rapid and reversible insertion and β-hydride elimination to isomerize 3-methylindene and 1-exo-methylene-indane, accounting for the isotopic distribution observed in the products. Mechanistic studies, including stoichiometric experiments, density functional theory calculations, and kinetic analysis, support a mechanism in which 2,3-alkene insertion into a cobalt hydride intermediate determines both the regio- and diastereoselectivity of the catalytic reaction. Synthetic applications of the indanyl boronate esters were demonstrated through the elaboration of the products to several examples of 1,3-disubstituted indanes, important carbocyclic structural motifs in both pharmacological and bioactive molecules." @default.
- W2969601412 created "2019-08-29" @default.
- W2969601412 creator A5027232517 @default.
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- W2969601412 creator A5051582648 @default.
- W2969601412 creator A5077963994 @default.
- W2969601412 creator A5087910041 @default.
- W2969601412 date "2019-08-20" @default.
- W2969601412 modified "2023-10-18" @default.
- W2969601412 title "Remote, Diastereoselective Cobalt-Catalyzed Alkene Isomerization–Hydroboration: Access to Stereodefined 1,3-Difunctionalized Indanes" @default.
- W2969601412 cites W1260922102 @default.
- W2969601412 cites W1911837735 @default.
- W2969601412 cites W1964284432 @default.
- W2969601412 cites W1964297120 @default.
- W2969601412 cites W1969858517 @default.
- W2969601412 cites W1971355114 @default.
- W2969601412 cites W1977462067 @default.
- W2969601412 cites W1978127915 @default.
- W2969601412 cites W1978890358 @default.
- W2969601412 cites W1986119632 @default.
- W2969601412 cites W1989917519 @default.
- W2969601412 cites W1995250651 @default.
- W2969601412 cites W1999785322 @default.
- W2969601412 cites W2002629749 @default.
- W2969601412 cites W2006630058 @default.
- W2969601412 cites W2008243054 @default.
- W2969601412 cites W2023167754 @default.
- W2969601412 cites W2024752439 @default.
- W2969601412 cites W2036121419 @default.
- W2969601412 cites W2041776698 @default.
- W2969601412 cites W2042767439 @default.
- W2969601412 cites W2043737037 @default.
- W2969601412 cites W2045952721 @default.
- W2969601412 cites W2070584942 @default.
- W2969601412 cites W2081521474 @default.
- W2969601412 cites W2082716360 @default.
- W2969601412 cites W2086885680 @default.
- W2969601412 cites W2091268948 @default.
- W2969601412 cites W2109726612 @default.
- W2969601412 cites W2110544193 @default.
- W2969601412 cites W2121382520 @default.
- W2969601412 cites W2128263034 @default.
- W2969601412 cites W2149950922 @default.
- W2969601412 cites W2153848081 @default.
- W2969601412 cites W2158491765 @default.
- W2969601412 cites W2161256103 @default.
- W2969601412 cites W2161550840 @default.
- W2969601412 cites W2171289933 @default.
- W2969601412 cites W2208099512 @default.
- W2969601412 cites W2232467577 @default.
- W2969601412 cites W2253330152 @default.
- W2969601412 cites W2260946417 @default.
- W2969601412 cites W2284217991 @default.
- W2969601412 cites W2291168385 @default.
- W2969601412 cites W2291919896 @default.
- W2969601412 cites W2296466350 @default.
- W2969601412 cites W2312521116 @default.
- W2969601412 cites W2317361287 @default.
- W2969601412 cites W2323527664 @default.
- W2969601412 cites W2324208632 @default.
- W2969601412 cites W2325231887 @default.
- W2969601412 cites W2326068625 @default.
- W2969601412 cites W2328705110 @default.
- W2969601412 cites W2328816656 @default.
- W2969601412 cites W2332144894 @default.
- W2969601412 cites W2379591351 @default.
- W2969601412 cites W2404975992 @default.
- W2969601412 cites W2468515422 @default.
- W2969601412 cites W2507307279 @default.
- W2969601412 cites W2521473510 @default.
- W2969601412 cites W2530709012 @default.
- W2969601412 cites W2531272945 @default.
- W2969601412 cites W2541343368 @default.
- W2969601412 cites W2551774833 @default.
- W2969601412 cites W2558902660 @default.
- W2969601412 cites W2560002048 @default.
- W2969601412 cites W2566916576 @default.
- W2969601412 cites W2571374444 @default.
- W2969601412 cites W2588389073 @default.
- W2969601412 cites W2589662445 @default.
- W2969601412 cites W2601190908 @default.
- W2969601412 cites W2601224882 @default.
- W2969601412 cites W2602529349 @default.
- W2969601412 cites W2605500166 @default.
- W2969601412 cites W2605604471 @default.
- W2969601412 cites W2608684199 @default.
- W2969601412 cites W2611496391 @default.
- W2969601412 cites W2658607595 @default.
- W2969601412 cites W2733660879 @default.
- W2969601412 cites W2735414732 @default.
- W2969601412 cites W2742183380 @default.
- W2969601412 cites W2745113775 @default.
- W2969601412 cites W2753033373 @default.
- W2969601412 cites W2757887969 @default.
- W2969601412 cites W2765813806 @default.
- W2969601412 cites W2766558529 @default.
- W2969601412 cites W2769452815 @default.
- W2969601412 cites W2770914334 @default.