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• W4310960151 endingPage "23126" @default.
• W4310960151 startingPage "23115" @default.
• W4310960151 abstract "This manuscript describes a mild, functional group tolerant, and metal-free C-H carboxylation that enables direct access to azole-2-carboxylic acids, followed by amide coupling in one pot. This demonstrates a significant expansion of the accessible chemical space of azole-2-amides, compared to previously known methodologies. Key to the described reactivity is the use of silyl triflate reagents, which serve as reaction mediators in C-H deprotonation and stabilizers of (otherwise unstable) azole carboxylic acid intermediates. A diverse azole substrate scope designed via machine-learning-guided analysis demonstrates the broad utility of the sequence. Density functional theory calculations provide detailed insights into the role of silyl triflates in the reaction mechanism. Transferrable applications of the protocol are successfully established: (i) A low pressure (CO2 balloon) option for synthesizing azole-2-carboxylic acids without the need for high-pressure equipment; (ii) the use of 13CO2 for the synthesis of labeled compounds; (iii) isocyanates as alternative electrophiles for direct C-H amidation; (iv) and the use of the developed chemistry in a 24 × 12 parallel synthesis workflow with a 90% library success rate. Fundamentally, the reported protocol expands the use of heterocycle C-H functionalization from late-stage functionalization applications toward its use in library synthesis. It provides general access to densely functionalized azole-2-carboxylic acid building blocks and demonstrates their one-pot diversification." @default.
• W4310960151 created "2022-12-21" @default.
• W4310960151 creator A5005944470 @default.
• W4310960151 creator A5050258489 @default.
• W4310960151 creator A5052930998 @default.
• W4310960151 creator A5061305059 @default.
• W4310960151 creator A5079405339 @default.
• W4310960151 date "2022-12-09" @default.
• W4310960151 modified "2023-10-16" @default.
• W4310960151 title "Accessing Diverse Azole Carboxylic Acid Building Blocks via Mild C–H Carboxylation: Parallel, One-Pot Amide Couplings and Machine-Learning-Guided Substrate Scope Design" @default.
• W4310960151 cites W1656095725 @default.
• W4310960151 cites W1975956870 @default.
• W4310960151 cites W1981921235 @default.
• W4310960151 cites W1985511422 @default.
• W4310960151 cites W1991915068 @default.
• W4310960151 cites W2001152439 @default.
• W4310960151 cites W2007558467 @default.
• W4310960151 cites W2024983608 @default.
• W4310960151 cites W2027600077 @default.
• W4310960151 cites W2028351186 @default.
• W4310960151 cites W2041340439 @default.
• W4310960151 cites W2044254542 @default.
• W4310960151 cites W2044258780 @default.
• W4310960151 cites W2052602206 @default.
• W4310960151 cites W2057027713 @default.
• W4310960151 cites W2057641806 @default.
• W4310960151 cites W2066874623 @default.
• W4310960151 cites W2068749447 @default.
• W4310960151 cites W2069887352 @default.
• W4310960151 cites W2071295790 @default.
• W4310960151 cites W2071418326 @default.
• W4310960151 cites W2101373633 @default.
• W4310960151 cites W2108355984 @default.
• W4310960151 cites W2108733419 @default.
• W4310960151 cites W2124947430 @default.
• W4310960151 cites W2126363023 @default.
• W4310960151 cites W2151114296 @default.
• W4310960151 cites W2163768766 @default.
• W4310960151 cites W2247581895 @default.
• W4310960151 cites W2286942279 @default.
• W4310960151 cites W2294606986 @default.
• W4310960151 cites W2310818325 @default.
• W4310960151 cites W2317144448 @default.
• W4310960151 cites W2328571531 @default.
• W4310960151 cites W2328665883 @default.
• W4310960151 cites W2333378312 @default.
• W4310960151 cites W2335578790 @default.
• W4310960151 cites W2339051409 @default.
• W4310960151 cites W2345162652 @default.
• W4310960151 cites W2389531102 @default.
• W4310960151 cites W2407040666 @default.
• W4310960151 cites W2509105246 @default.
• W4310960151 cites W2523833102 @default.
• W4310960151 cites W2612897480 @default.
• W4310960151 cites W2729972564 @default.
• W4310960151 cites W2741451454 @default.
• W4310960151 cites W2755338181 @default.
• W4310960151 cites W2755677754 @default.
• W4310960151 cites W2767593617 @default.
• W4310960151 cites W2779319614 @default.
• W4310960151 cites W2799656331 @default.
• W4310960151 cites W2799660157 @default.
• W4310960151 cites W2806607221 @default.
• W4310960151 cites W2806841040 @default.
• W4310960151 cites W2807784890 @default.
• W4310960151 cites W2883408915 @default.
• W4310960151 cites W2902770012 @default.
• W4310960151 cites W2906145236 @default.
• W4310960151 cites W2915398515 @default.
• W4310960151 cites W2946764827 @default.
• W4310960151 cites W2947617881 @default.
• W4310960151 cites W2949753031 @default.
• W4310960151 cites W2952251456 @default.
• W4310960151 cites W2954750231 @default.
• W4310960151 cites W2975254165 @default.
• W4310960151 cites W2999655853 @default.
• W4310960151 cites W3012519883 @default.
• W4310960151 cites W3016762617 @default.
• W4310960151 cites W3020447607 @default.
• W4310960151 cites W3095971278 @default.
• W4310960151 cites W3127803327 @default.
• W4310960151 cites W3128724272 @default.
• W4310960151 cites W3129191976 @default.
• W4310960151 cites W3134114745 @default.
• W4310960151 cites W3159938363 @default.
• W4310960151 cites W3168224616 @default.
• W4310960151 cites W3180015469 @default.
• W4310960151 cites W3216063409 @default.
• W4310960151 cites W4211051003 @default.
• W4310960151 cites W4211188528 @default.
• W4310960151 cites W4214911431 @default.
• W4310960151 cites W4220799686 @default.
• W4310960151 cites W4237624288 @default.
• W4310960151 cites W4237630354 @default.
• W4310960151 cites W4252659795 @default.
• W4310960151 cites W4281790623 @default.
• W4310960151 cites W4306163774 @default.
• W4310960151 doi "https://doi.org/10.1021/jacs.2c10557" @default.

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