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- W2744332602 endingPage "4048" @default.
- W2744332602 startingPage "4028" @default.
- W2744332602 abstract "The reaction of FcCH 2 OH with chlorophosphates gave ferrocenyl phosphates FcCH 2 OP(O)(OR) 2 [Fc = Fe(η 5 ‐C 5 H 5 )(η 4 ‐C 5 H 4 )], which readily separate into phosphate anions and ferrocenyl carbo‐cations. The latter species undergoes consecutive reactions, for example, electrophilic aromatic substitutions. When nitriles, instead of alcohols, are treated with FcLi or t BuLi and chlorophosphates, chiral‐pool based ferrocenylimino phosphoramidates Fc‐CR=N‐P(O)(OR*) 2 are formed, which are promising candidates for anionic homo phospho‐Fries rearrangements. Moreover, the sterically demanding chiral chlorophosphate with R* enabled oxidative couplings of the imines to form a diferrocenylazine. Similarly, the reaction of Fc–Li with 9‐anthrylnitrile produced a 10‐ferrocenyl‐substituted product, contrary to a reaction at the C≡N functionality. A planar‐chiral ortho ‐P(S)Ph 2 ‐functionalized ferrocenylmethanol also gave carbo‐cations under acidic conditions. These species can be sulfurized in a unique way giving thio ethers, whereby the in situ formed 1,2‐P(S)Ph 2 ,CH 2 + ferrocene cation acts as the sulfur and electron source. However, lowering the substrate concentration prevents sulfur migration, resulting in electrophilic substitution reactions with aromatic solvents. Planar‐chiral ferrocenylmethyl thio or anisyl derivatives were applied as ligands in Pd‐catalyzed Suzuki–Miyaura C , C cross‐couplings for the atroposelective synthesis of hindered biaryls with up to 26 % ee at low catalyst loadings (1 mol‐% Pd)." @default.
- W2744332602 created "2017-08-17" @default.
- W2744332602 creator A5015080148 @default.
- W2744332602 creator A5039877065 @default.
- W2744332602 creator A5088536141 @default.
- W2744332602 date "2017-09-13" @default.
- W2744332602 modified "2023-10-16" @default.
- W2744332602 title "(Planar‐Chiral) Ferrocenylmethanols: From Anionic Homo Phospho‐Fries Rearrangements to α‐Ferrocenyl Carbenium Ions" @default.
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