An unusual reaction of α-alkoxyphosphonium salts with Grignard reagents under an O2 atmosphere.
نویسندگان
چکیده
An unusual and novel reaction of α-alkoxyphosphonium salts, generated from O,O-acetals and Ph(3)P, with Grignard reagents under an O(2) atmosphere afforded alcohols in moderate to high yields. It was clarified by isotopic labelling experiments that the reaction proceeded via a novel radical pathway.
منابع مشابه
Air-assisted addition of grignard reagents to olefins. A simple protocol for a three-component coupling process yielding alcohols.
Silylmethyl, tertiary-alkyl, alkenyl, and aryl Grignard reagents underwent intermolecular addition to olefins, such as styrenes, conjugated dienes, and enynes under an air atmosphere to give homologated alcohols. For example, (trimethylsilyl)methylmagnesium chloride and alpha-methylstyrene in ether at room temperature under dry air directly furnished 2-phenyl-4-(trimethylsilyl)-2-butanol in goo...
متن کاملHigh-Yield Alkylation and Arylation of Graphene via Grignard Reaction with Fluorographene
C functionalization of graphene significantly broadens its application potential via tuning its electronic and surface properties. Therefore, a wide range of dry and wet chemistry approaches have been developed for graphene functionalization. Despite recent progress in this field, covalent modification of graphene is still hampered by its low reactivity. Moreover, the reactivity depends on the ...
متن کاملCopper-free arylation of 3,3-disubstituted allylic halides with triazene-softened aryl Grignard reagents.
A copper-free allylic arylation reaction between 3,3-disubstituted allylic halides and triazene-softened aryl Grignard reagents has been developed. This protocol presents a direct and efficient way to construct both α- or γ-isomers with high regioselectivity under environmentally benign conditions. Various functional groups can be tolerated in the reaction and the products are of high value for...
متن کاملManganese- or iron-catalyzed homocoupling of grignard reagents using atmospheric oxygen as an oxidant.
Homocoupling reactions of aryl, alkenyl, and alkynyl Grignard reagents are an easy and efficient access to symmetrical dior polyaromatic, olefinic, or acetylenic conjugated compounds. The potential applications of such compounds in optical materials, molecular devices, and organic conductors are well-recognized.1 Therefore, for large-scale applications, it is interesting to develop more conveni...
متن کاملEfficient synthesis of aryl fluorides.
Selective functionalization reactions of aromatic and heteroaromatic halides with carbon, oxygen, and nitrogen nucleophiles have attracted much attention in the last decades. In addition to typical metal-catalyzed coupling reactions, direct functionalization of aryl halides through the formation of Grignard reagents offer new ways for the efficient construction of biologically interesting carbo...
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:
- Chemical communications
دوره 47 35 شماره
صفحات -
تاریخ انتشار 2011