Decarboxylative, Radical C-C Bond Formation with Alkyl or Aryl Carboxylic Acids: Recent Advances

Decarboxylative, Radical C-C Bond Formation with Alkyl or Aryl Carboxylic Acids: Recent Advances
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烷基或芳基羧酸脱羧、自由基 C-C 键形成:最新进展

DOI:
10.1055/a-2081-1830
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发表时间:
2023
期刊:
Synthesis
影响因子:
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通讯作者:
Cresswell A
Cresswell A
中科院分区:
--
文献类型:
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作者:
Cresswell A

文献摘要

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羧酸作为天然衍生或人造化学原料的普遍存在,刺激了有机合成中强大的脱羧C-C键形成转化的发展。羧酸不仅受益于广泛的商业可用性,而且在过渡金属催化的交叉偶联中是有机卤化物或有机金属试剂的稳定替代品。羧酸(或其衍生物)提供碳中心自由基的开壳反应性被证明对合成化学具有变革性,使具有精细化学选择性的新颖策略级C(sp3) -C键断开成为可能。这篇简短的综述将总结这一不断扩大的领域的几项最新进展2改进的脱羧芳基化反应3羧酸与脂肪族溴化物的sp3 - sp3交叉偶联反应4羧酸与脂肪族醇和胺的sp3 - sp3交叉偶联反应5羧酸的双脱羧反应sp3 - sp3交叉偶联反应6(杂)芳基羧酸脱羧形成C-C键7结论
The ubiquity of carboxylic acids as naturally derived or man-made chemical feedstocks has spurred the development of powerful, decarboxylative C–C bond-forming transformations for organic synthesis. Carboxylic acids benefit not only from extensive commercial availability, but are stable surrogates for organohalides or organometallic reagents in transition-metal-catalysed cross-coupling. Open shell reactivity of carboxylic acids (or derivatives thereof) to furnish carbon-centred radicals is proving transformative for synthetic chemistry, enabling novel and strategy-level C(sp3)–C bond disconnections with exquisite chemoselectivity. This short review will summarise several of the latest advances in this ever-expanding area.1 Introduction2 Improved Decarboxylative Arylations3 sp3–sp3Cross-Coupling of Carboxylic Acids with Aliphatic Bromides4 sp3–sp3Cross-Coupling of Carboxylic Acids with Aliphatic Alcohols and Amines5 Doubly Decarboxylative sp3–sp3Cross-Coupling of Carboxylic Acids6 Decarboxylative C–C Bond Formation from (Hetero)aryl Carboxylic Acids7 Conclusions