Anti-Markovnikov oxidation and hydration of terminal olefins.
نویسندگان
چکیده
Efficient syntheses of aldehydes and primary alcohols from terminal olefins are critical to the chemical laboratory and industry. Heavy emphasis has been placed on regioselective olefin functionalization in recent decades. This perspective mainly focuses on advances in the Wacker-type oxidation and tandem hydration of terminal olefins with anti-Markovnikov selectivity.
منابع مشابه
Primary alcohols from terminal olefins: formal anti-Markovnikov hydration via triple relay catalysis.
Alcohol synthesis is critical to the chemical and pharmaceutical industries. The addition of water across olefins to form primary alcohols (anti-Markovnikov olefin hydration) would be a broadly useful reaction but has largely proven elusive; an indirect hydroboration/oxidation sequence requiring stoichiometric borane and oxidant is currently the most practical methodology. Here, we report a mor...
متن کاملFormal Anti-Markovnikov Hydroamination of Terminal Olefins.
A new strategy to access linear amines from terminal olefin precursors is reported. This two-step, one-pot hydroamination methodology employs sequential oxidation and reduction catalytic cycles. The formal hydroamination transformation proceeds with excellent regioselectivity, and only the anti-Markovnikov product is observed. Up to 70% yield can be obtained from styrenes or aliphatic olefins a...
متن کاملCatalytic Anti-Markovnikov Transformations of Hindered Terminal Alkenes Enabled by Aldehyde-Selective Wacker-Type Oxidation.
A new strategy for the functionalization of sterically hindered terminal olefins is reported. Alkenes bearing quaternary carbons at the allylic or homoallylic position are readily oxidized to the corresponding aldehydes by palladium/copper/nitrite catalysis. A broad range of functional groups including esters, nitriles, silyl ethers, vinylogous esters, ketones, lactones, and β-ketoesters are to...
متن کاملPalladium-assisted multicomponent cyclization of aromatic aldehydes, arylamines and terminal olefins under molecular oxygen: an assembly of 1,4-dihydropyridines.
The palladium-assisted one-pot three-component reactions of aldehydes, amines and olefins proceeded smoothly to give 2,6-unsubstituted 1,4-dihydropyridines (1,4-DHPs) using molecular oxygen as a sole oxidant. It also provides efficient Pd-catalyzed aerobic oxidation access to the anti-Markovnikov oxidative amination products of olefins from primary aromatic amines and alkenes. The method is ato...
متن کاملNovel anti-Markovnikov regioselectivity in the Wacker reaction of styrenes.
The Wacker reaction is one of the longest known palladium-catalysed organic transformations, and in the vast majority of cases proceeds with Markovnikov regioselectivity. Palladium(II)-mediated oxidation of styrenes was examined and in the absence of reoxidants was found to proceed in an anti-Markovnikov sense, giving aldehydes. Studies on the mechanism of this unusual transformation were carri...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Dalton transactions
دوره 43 19 شماره
صفحات -
تاریخ انتشار 2014