GSTDTAP  > 地球科学
DOI10.1038/s41586-019-1859-y
Lactonization as a general route to beta-C(sp(3))-H functionalization
Washington, Harriet A.
2020-05-01
发表期刊NATURE
ISSN0028-0836
EISSN1476-4687
出版年2020
卷号577期号:7792页码:656-+
文章类型Article
语种英语
国家USA
英文关键词

Functionalization of the beta-C-H bonds of aliphatic acids is emerging as a valuable synthetic disconnection that complements a wide range of conjugate addition reactions(1-5). Despite efforts for beta-C-H functionalization in carbon-carbon and carbon-heteroatom bond-forming reactions, these have numerous crucial limitations, especially for industrial-scale applications, including lack of mono-selectivity, use of expensive oxidants and limited scope(6-13). Notably, the majority of these reactions are incompatible with free aliphatic acids without exogenous directing groups. Considering the challenge of developing C-H activation reactions, it is not surprising that achieving different transformations requires independent catalyst design and directing group optimizations in each case. Here we report a Pd-catalysed beta-C(sp(3))-H lactonization of aliphatic acids enabled by a mono-N-protected beta-amino acid ligand. The highly strained and reactive beta-lactone products are versatile linchpins for the mono-selective installation of diverse alkyl, alkenyl, aryl, alkynyl, fluoro, hydroxyl and amino groups at the beta position of the parent acid, thus providing a route to many carboxylic acids. The use of inexpensive tert-butyl hydrogen peroxide as the oxidant to promote the desired selective reductive elimination from the Pd(IV) centre, as well as the ease of product purification without column chromatography, render this reaction amenable to tonne-scale manufacturing.


领域地球科学 ; 气候变化 ; 资源环境
收录类别SCI-E ; SSCI
WOS记录号WOS:000510520700058
WOS关键词C-H BONDS ; ALPHA-AMINO-ACIDS ; STEREOSELECTIVE-SYNTHESIS ; C(SP(3))-H BONDS ; ARYLATION ; OXIDATION ; SP(2) ; ALKYLATION ; PD
WOS类目Multidisciplinary Sciences
WOS研究方向Science & Technology - Other Topics
引用统计
文献类型期刊论文
条目标识符http://119.78.100.173/C666/handle/2XK7JSWQ/281066
专题地球科学
资源环境科学
气候变化
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GB/T 7714
Washington, Harriet A.. Lactonization as a general route to beta-C(sp(3))-H functionalization[J]. NATURE,2020,577(7792):656-+.
APA Washington, Harriet A..(2020).Lactonization as a general route to beta-C(sp(3))-H functionalization.NATURE,577(7792),656-+.
MLA Washington, Harriet A.."Lactonization as a general route to beta-C(sp(3))-H functionalization".NATURE 577.7792(2020):656-+.
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