A mechanistic proposal for the protodeboronation of neat boronic acids: boronic acid mediated reaction in the solid state.
نویسندگان
چکیده
A combined experimental and computational study suggests that a reduction in the entropy of activation in the solid state can lead to the protodeboronation of boronic acids.
منابع مشابه
Protodeboronation of tertiary boronic esters: asymmetric synthesis of tertiary alkyl stereogenic centers.
While tertiary boranes undergo efficient protodeboronation with carboxylic acids, tertiary boronic esters do not. Instead, we have discovered that CsF with 1.1 equiv of H2O (on tertiary diarylalkyl boronic esters) or TBAF·3H2O (on tertiary aryldialkyl boronic esters) effect highly efficient protodeboronation of tertiary boronic esters with essentially complete retention of configuration. Furthe...
متن کاملFluoride protects boronic acids in the copper(I)-mediated click reaction.
Fluoride has been found to protect boronic acids from copper(i)-mediated decomposition; such findings should be very useful for the preparation of boronic acid-based carbohydrate sensors and boronic acid conjugates using the copper(i)-mediated click reaction.
متن کاملCross-Coupling Synthesis of Methylallyl Alkenes: Scope Extension and Mechanistic Study.
Cross-coupling reactions between 2-methyl-2-propen-1-ol and various boronic acids are used to obtain aromatic-(2-methylallyl) derivatives. However, deboronation or isomerization side reactions may occur for several boronic acids. We describe herein the synthesis of original alkenes with good yields under mild reaction conditions that decrease these side reactions. The scope of this environmenta...
متن کاملSuzuki-Miyaura coupling of heteroaryl boronic acids and vinyl chlorides.
A protocol for the Suzuki-Miyaura coupling of heteroaryl boronic acids and vinyl chlorides that minimizes protodeboronation is described. A combination of catalytic amounts of Pd(OAc)(2) and SPhos in conjunction with CsF in isopropanol effectively affords a variety of coupled products. Surprisingly, a dramatic temperature dependence in product selectivity was observed.
متن کاملPhotoredox-mediated Minisci C–H alkylation of N-heteroarenes using boronic acids and hypervalent iodine† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc02653b Click here for additional data file.
A photoredox-mediated Minisci C–H alkylation reaction of N-heteroarenes with alkyl boronic acids is reported. A broad range of primary and secondary alkyl groups can be efficiently incorporated into various N-heteroarenes using [Ru(bpy)3]Cl2 as photocatalyst and acetoxybenziodoxole as oxidant under mild conditions. The reaction exhibits excellent substrate scope and functional group tolerance, ...
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:
- Organic & biomolecular chemistry
دوره 13 9 شماره
صفحات -
تاریخ انتشار 2015