- Visible-light-promoted site-specific and diverse functionalization of a c(sp3)-c(sp3) bond adjacent to an arene
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We report here a strategy for inert C-C bond functionalization. Site-specific cleavage and functionalization of a saturated C(sp3)-C(sp3) bond via a visible-light-induced radical process have been achieved. The general features of this reaction are as follows. (1) Both linear and cyclic C(sp3)-C(sp3) bonds with a vicinal arene can be specifically functionalized. (2) One carbon is converted into a ketone, and another can be tunably converted into nitrile, peroxide, or halide. (3) The typical conditions include 1.0 mol % of Ru(bpy)3Cl2, 1.0 or 5.0 equiv of Zhdankin reagent, white CFL (24 W), open flask, and room temperature. These reactions offer powerful tools to modify carbon skeletons that are intractable by conventional methods. Good selectivity and functional group tolerance, together with mild and open air conditions, make these transformations valuable and attractive.
- Fang, Fang,Liu, Zhong-Quan,Sun, Minzhi,Wang, Nengyong,Wang, Yaxin,You, Huichao,Zhao, Jianyou
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p. 6603 - 6612
(2020/07/27)
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- Palladium-Catalyzed Carbonylative Synthesis of Benzyl Benzoates Employing Benzyl Formates as Both CO Surrogates and Benzyl Alcohol Sources
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An efficient and convenient palladium-catalyzed carbonylation reaction for the synthesis of benzyl benzoates from aryl bromides has been developed. Benzyl formates have been explored as a new type of efficient and useful CO sources and also reaction partners. A wide range of benzyl benzoates was obtained in good to excellent yields.
- Lai, Ming,Qi, Xinxin,Wu, Xiao-Feng
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supporting information
p. 3776 - 3778
(2019/06/24)
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- Oxidative debenzylation of N-benzyl amides and O-benzyl ethers using alkali metal bromide
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The oxidative debenzylation of N-benzyl amides and O-benzyl ethers was promoted with high efficiency by a bromo radical formed through the oxidation of bromide from alkali metal bromide under mild conditions. This reaction provided the corresponding amides from N-benzyl amides and carbonyl compounds from O-benzyl ethers in high yields.
- Moriyama, Katsuhiko,Nakamura, Yu,Togo, Hideo
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supporting information
p. 3812 - 3815
(2014/08/05)
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- A Convenient Protocol for the Esterification of Carboxylic Acids with Alcohols in the Presence of di-t-Butyl Dicarbonate
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Stoichiometric mixtures of carboxylic acids and primary or secondary alkyl alcohols are cleanly converted into their corresponding esters by treatment with di-t-butyl dicarbonate [(BOC)2O] in the presence of catalytic amounts of N,N′-dimethylaminopyridine (DMAP). This convenient procedure provides a general access to a broad variety of esters including those bearing highly sensitive functional groups such as phenol esters or BOC-groups. Purification of the products is particularly easy since the byproducts t-BuOH and CO2 are volatile - a great advantage over the standard DCC/DMAP method.
- Goo?en, Lukas J.,D?hring, Arno
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p. 263 - 266
(2007/10/03)
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- Lewis Acids as Highly Efficient Catalysts for the Decarboxylative Esterification of Carboxylic Acids with Dialkyl Dicarbonates
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Mild Lewis acids such as Mg(ClO4)2 show a new level of catalytic activity for the decarboxylative esterification of carboxylic acids with commercially available dialkyl dicarbonates. In the presence of as little as one mol % Mg(ClO4)2 catalyst, carboxylic acids can thus easily and near quantitatively be protected at room temperature, e.g., as methyl, benzyl, or t-butyl esters. Only volatile by-products are released so that the purification of the products is particularly easy. Many sensitive functionalities are tolerated, including even phenol esters, or free hydroxy and BOC groups.
- Goossen,Doehring
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p. 943 - 947
(2007/10/03)
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- Amidinophenol derivatives
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Amidinophenol derivatives of the formula (I): STR1 wherein R1 and R2 are (i) H, (ii) C1-4 alkyl, (iii) C1-4 alkoxy, (iv) C2-5 acyl, (v) halogen, (vi) NO2, (vii) benzoyl, (viii) COOR4 (in which R4 is C1-3 alkyl); A is bond, C1-4 alkylene, --C(R5)=C(R6)-- (in which R5 and R6 are H or C1-4 alkyl; R3 is (i) CON(R7)(R8), (ii) CON(R9)--CH(R7)(R8) or (iii) STR2 in which STR3 is 4-7 membered, mono-cyclic hetero ring containing 1 or 2 N atom; R10 is H, C7-10 phenylalkyl or COOR13 (in which R13 is H, C1-4 alkyl or C7-10 phenylalkyl)); with the proviso that (i) both R7 and R8 do not represent hydrogen at the same time, and (ii) when at least one group in R7, R8 and R9 represents the group containing t-butyl ester, the other groups do not represent tile group containing carboxy; or an acid-addition salt thereof, have inhibitory activities on PLA2 and on various proteases such as trypsin, plasmin, thrombin, kallikrein, especially trypsin, and are useful for the prevention and/or the treatment of various inflammatory diseases, allergic diseases, disseminated intravascular coagulation, pancreatitis, severity in pancreatitis and multiple organ failure.
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