FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2160633522> ?p ?o ?g. }

• W2160633522 endingPage "6299" @default.
• W2160633522 startingPage "6285" @default.
• W2160633522 abstract "Abstract Access to highly enantioenriched planar chiral [Cr(5‐bromonaphthalene)(CO) 3 ] ( 6 ), [Ru(η 5 ‐C 5 R 5 )(5‐bromonaphthalene)][PF 6 ] ( 42 ) and [Ru(η 5 ‐C 5 R 5 )(4‐bromoindene)] ( 44 ) was sought using asymmetric hydrogenolysis of [Cr(5,8‐dibromonaphthalene)(CO) 3 ] ( 5 ), [Ru(η 5 ‐C 5 R 5 )(5,8‐dibromonaphthalene)] ( 39 ) and [Ru(η 5 ‐C 5 R 5 )(4,7‐dibromoindene)] ( 40 ), respectively. Initial efforts focused on the chromium complex 5 . Pd 0 catalysts with dimethoxyethane as the solvent and LiBH 4 or NaBH 3 CN as a hydride source worked best. Nineteen chiral bidentate phosphorus ligands were screened in this reaction. Asymmetric induction was low to modest with product ee ’s in the range of 4 to 52 % and yields of 6 of up to 70 %. Chiral phosphoramidite ligands proved superior and a bulky ligand derived from a Whitesell amine and 3,3′‐diphenyl‐binaphtol afforded 6 with an ee of 97 %. The high enantioselectivity is largely due to the initial desymmetrization reaction though kinetic resolution also plays an important role as shown by the determination of a selectivity factor s =8.5 at −10 ° C. Initially high ligand loadings (4 equiv/Pd) were necessary to achieve good asymmetric induction. This could be traced to the trapping of the chiral ligand by borane formed in the reaction. Addition of 1,4‐diazabicyclo[2.2.2]octane (DABCO) suppressed this, and its addition led to the use of Pd and chiral ligand in a 1:1.2 ratio. Asymmetric hydrogenolysis of cationic dibromonaphthalene and neutral dibromoindenyl complexes of Ru cyclopentadienyl complexes was investigated and afforded the following results: [RuCp(5‐bromonaphthalene)][PF 6 ] ( 39 a ; 75 %, 90 % ee ), [RuCp*(5‐bromonaphthalene)] [PF 6 ] ( 39 b ; 88 %, 99 % ee ), [RuCp(4‐bromoindenyl)] ( 44 a ; 72 %, 96 % ee ), and [RuCp*(4‐bromoindenyl)] ( 44 b ; 62 %, 68 % ee )." @default.
• W2160633522 created "2016-06-24" @default.
• W2160633522 creator A5014838503 @default.
• W2160633522 creator A5020737851 @default.
• W2160633522 creator A5024683611 @default.
• W2160633522 creator A5026346376 @default.
• W2160633522 creator A5042241381 @default.
• W2160633522 creator A5044740424 @default.
• W2160633522 creator A5083777372 @default.
• W2160633522 creator A5089770730 @default.
• W2160633522 date "2010-05-25" @default.
• W2160633522 modified "2023-10-18" @default.
• W2160633522 title "Asymmetric Catalytic Hydrogenolysis of ArylHalide Bonds in Fused Arene Chromium and Ruthenium Complexes" @default.
• W2160633522 cites W1436391810 @default.
• W2160633522 cites W1534077339 @default.
• W2160633522 cites W1559064942 @default.
• W2160633522 cites W1964603524 @default.
• W2160633522 cites W1964807563 @default.
• W2160633522 cites W1967641942 @default.
• W2160633522 cites W1967835930 @default.
• W2160633522 cites W1968660812 @default.
• W2160633522 cites W1970629886 @default.
• W2160633522 cites W1970791995 @default.
• W2160633522 cites W1972634598 @default.
• W2160633522 cites W1973053405 @default.
• W2160633522 cites W1973420096 @default.
• W2160633522 cites W1974713831 @default.
• W2160633522 cites W1977048131 @default.
• W2160633522 cites W1981647051 @default.
• W2160633522 cites W1984023726 @default.
• W2160633522 cites W1984910002 @default.
• W2160633522 cites W1985040070 @default.
• W2160633522 cites W1988015502 @default.
• W2160633522 cites W1991106972 @default.
• W2160633522 cites W1992556016 @default.
• W2160633522 cites W1997853473 @default.
• W2160633522 cites W2001471746 @default.
• W2160633522 cites W2008197307 @default.
• W2160633522 cites W2012341731 @default.
• W2160633522 cites W2013136436 @default.
• W2160633522 cites W2013171720 @default.
• W2160633522 cites W2020086770 @default.
• W2160633522 cites W2024270887 @default.
• W2160633522 cites W2025288494 @default.
• W2160633522 cites W2028318563 @default.
• W2160633522 cites W2030900040 @default.
• W2160633522 cites W2031702350 @default.
• W2160633522 cites W2032047349 @default.
• W2160633522 cites W2032593703 @default.
• W2160633522 cites W2033466285 @default.
• W2160633522 cites W2034243252 @default.
• W2160633522 cites W2036733274 @default.
• W2160633522 cites W2037690684 @default.
• W2160633522 cites W2040354285 @default.
• W2160633522 cites W2040368043 @default.
• W2160633522 cites W2041594924 @default.
• W2160633522 cites W2042960908 @default.
• W2160633522 cites W2044362459 @default.
• W2160633522 cites W2044831737 @default.
• W2160633522 cites W2045269944 @default.
• W2160633522 cites W2045897873 @default.
• W2160633522 cites W2046223932 @default.
• W2160633522 cites W2046410208 @default.
• W2160633522 cites W2046890918 @default.
• W2160633522 cites W2050866142 @default.
• W2160633522 cites W2051542700 @default.
• W2160633522 cites W2057444581 @default.
• W2160633522 cites W2059890956 @default.
• W2160633522 cites W2059997435 @default.
• W2160633522 cites W2060778885 @default.
• W2160633522 cites W2062487750 @default.
• W2160633522 cites W2067747700 @default.
• W2160633522 cites W2070151057 @default.
• W2160633522 cites W2071373132 @default.
• W2160633522 cites W2074133859 @default.
• W2160633522 cites W2076148386 @default.
• W2160633522 cites W2076784243 @default.
• W2160633522 cites W2077759327 @default.
• W2160633522 cites W2078250691 @default.
• W2160633522 cites W2079398245 @default.
• W2160633522 cites W2080379656 @default.
• W2160633522 cites W2080393787 @default.
• W2160633522 cites W2080831153 @default.
• W2160633522 cites W2082263875 @default.
• W2160633522 cites W2083693692 @default.
• W2160633522 cites W2085121368 @default.
• W2160633522 cites W2087584441 @default.
• W2160633522 cites W2092054085 @default.
• W2160633522 cites W2095434006 @default.
• W2160633522 cites W2106852370 @default.
• W2160633522 cites W2108404924 @default.
• W2160633522 cites W2110511000 @default.
• W2160633522 cites W2111712170 @default.
• W2160633522 cites W2117529128 @default.
• W2160633522 cites W2124051004 @default.
• W2160633522 cites W2135595396 @default.
• W2160633522 cites W2141286236 @default.
• W2160633522 cites W2142637881 @default.

• next