Direct Carbocyclizations of Benzoic Acids: Catalyst-Controlled Synthesis of Cyclic Ketones and the Development of Tandem aHH (acyl Heck-Heck) Reactions

Kelsey C. Miles; Chi Chip Le; James P. Stambuli

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Direct Carbocyclizations of Benzoic Acids: Catalyst-Controlled Synthesis of Cyclic Ketones and the Development of Tandem aHH (acyl Heck-Heck) Reactions

机译：苯甲酸的直接碳环化：催化剂控制的环酮的合成和串联aHH（酰基Heck-Heck）反应的发展

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The formation of exo-methylene indanones and indenones from simple ortho-allyl benzoic acid derivatives has been developed. Selective formation of the indanone or indenone products in these reactions is controlled by choice of ancillary ligand. This new process has a low environmental footprint as the products are formed in high yields using low catalyst loadings, while the only stoichiometric chemical waste generated from the reactants in the transformation is acetic acid. The conversion of the active cyclization catalyst into the Hermman-Beller palladacycle was exploited in a one-pot tandem acyl Heck- Heck (aHH) reaction, and utilized in the synthesis of donepezil.

机译：已经开发了由简单的邻烯丙基苯甲酸衍生物形成外亚甲基茚满酮和茚满的方法。在这些反应中茚满酮或茚满酮产物的选择性形成是通过选择辅助配体来控制的。这种新工艺具有较低的环境足迹，因为使用低催化剂负载量可以高收率形成产物，而转化中反应物产生的唯一化学计量的化学废物是乙酸。活性环化催化剂向Hermman-Beller palladacycle的转化被用于一锅串联的酰基Heck-Heck（aHH）反应中，并用于多奈哌齐的合成。

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《Chemistry: A European journal》 |2014年第36期|共4页
作者
Kelsey C. Miles; Chi Chip Le; James P. Stambuli;
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正文语种 eng
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carboxylic acids; catalysis; cyclization; green chemistry; palladium;

机译：羧酸;催化;环化;绿色化学;钯;

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1. Direct Carbocyclizations of Benzoic Acids: Catalyst-Controlled Synthesis of Cyclic Ketones and the Development of Tandem aHH (acyl Heck-Heck) Reactions [J] . Kelsey C. Miles, Chi Chip Le, James P. Stambuli Chemistry: A European journal . 2014,第36期

机译：苯甲酸的直接碳环化：催化剂控制的环酮的合成和串联aHH（酰基Heck-Heck）反应的发展
2. Use of unprotected amino acids in metal-free tandem radical cyclization reactions: divergent synthesis of 6-alkyl/acyl phenanthridines [J] . Lu Shi-Chao, Li Hong-Shuang, Gong Ya-Ling, RSC Advances . 2017,第88期

机译：在无保护的氨基酸在无保护的氨基酸在无保护型串联自由基环化反应中：发散合成6-烷基/酰基菲尼斯
3. Use of unprotected amino acids in metal-free tandem radical cyclization reactions: divergent synthesis of 6-alkyl/acyl phenanthridines [J] . Shi-Chao Lu, Hong-Shuang Li, Ya-Ling Gong, RSC Advances . 2017,第88期

机译：在无金属串联自由基环化反应中使用未保护的氨基酸：6-烷基/酰基菲啶的发散合成
4. Direct Sensitive Simultaneous Determination of Fluorinated Benzoic Acids in Oil Reservoir Waters by Ultra High-Performance Liquid Chromatography - Tandem Mass Spectrometry [C] . Coralie Serres-Piole, Ryszard Iobinski, Navid Moradi-Tehrani, American Society for Mass Spectrometry Conference on Mass Spectrometry and Allied Topics . 2011

机译：超高效液相色谱法直接敏感同时测定油藏水中氟化苯甲酸 - 串联质谱法
5. Part I. Application of 2-hydroxymethylacrylic acid, a product of Baylis-Hillman reaction, for the synthesis of novel N-backbone-to-side-chain cyclic peptide analogs: Strategies and side reactions. Part II. Synthesis and biological activities of chimeric bioactive peptides featuring amino acids coupled to 4-anilino-n-phenethyl-piperidine. [D] . Petrov, Ravil Rashitovich. 2007

机译：第一部分。Baylis-Hillman反应产物2-羟甲基丙烯酸在合成新型N骨架至侧链环状肽类似物中的应用：策略和副反应。第二部分具有与4-苯胺基-n-苯乙基-哌啶偶联的氨基酸的嵌合生物活性肽的合成和生物活性。
6. Aryl Ketone Synthesis via Tandem Orthoplatinated Triarylphosphite-Catalyzed Addition Reactions of Arylboronic Acids with Aldehydes Followed by Oxidation [O] . Yuan-Xi Liao, Qiao-Sheng Hu -1

机译：通过芳基硼酸与醛的串联Orthoplatinated三芳基亚磷酸酯催化加成反应的芳基酮的合成之后进行氧化
7. Convergent methods for synthesizing rings in the context of natural product synthesis: I. Development of a tandem Stille-oxa-electrocyclization reaction, and progress toward the total synthesis of saudin. II. Development of the direct acyl-alkylation of arynes, and its application toward the total synthesis of amurensinine [O] . Tambar Uttam Krishan 2006

机译：在天然产物合成的背景下合成环的收敛方法：I。串联stille-oxa-电环化反应的开发，以及对saudin全合成的进展。 II。炔烃直接酰基烷基化的研究进展及其在氨苄西林全合成中的应用

Direct Carbocyclizations of Benzoic Acids: Catalyst-Controlled Synthesis of Cyclic Ketones and the Development of Tandem aHH (acyl Heck-Heck) Reactions

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