Pd-Catalysed direct C(sp2)-H fluorination of aromatic ketones: concise access to anacetrapib

被引：14

作者：

Wu, Qiuzi ^{[1
]}

Mao, Yang-Jie ^{[1
]}

Zhou, Kun ^{[1
]}

Wang, Shuang ^{[1
]}

Chen, Lei ^{[1
]}

Xu, Zhen-Yuan ^{[1
]}

Lou, Shao-Jie ^{[1
]}

Xu, Dan-Qian ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Key Lab Green Pesticides & Cleaner Prod Technol Z, State Key Lab Breeding Base Green Chem Synth Tech, Catalyt Hydrogenat Res Ctr, Hangzhou 310014, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 37期

基金：

中国博士后科学基金;

关键词：

LATE-STAGE FLUORINATION; C-H FUNCTIONALIZATION; WEAK-COORDINATION; BOND ACTIVATION; NEXT-GENERATION; ARYLATION; PHARMACEUTICALS; VERSATILE; ACIDS; MILD;

D O I：

10.1039/d1cc01047f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Pd-cataylsed direct ortho-C(sp(2))-H fluorination of aromatic ketones has been developed for the first time. The reaction features good regioselectivity and simple operations, constituting an alternative shortcut to access fluorinated ketones. A concise synthesis of anacetrapib has also been achieved by using late-stage C-H fluorination as a key step.

引用

页码：4544 / 4547

页数：4

共 65 条

[1] [Anonymous], 2011, Organization Letter
[2] [Anonymous], Chemical Reviews
[3] [Anonymous], J MED CHEM
[4] [Anonymous], Nat. Chem.
[5] [Anonymous], RSC ADV
[6] Synthesis and Reactivity of a Mono-σ-Aryl Palladium(IV) Fluoride Complex
Ball, Nicholas D.
Sanford, Melanie S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) : 3796 - +
[7] Organic synthesis provides opportunities to transform drug discovery
Blakemore, David C.
Castro, Luis
Churcher, Ian
Rees, David C.
Thomas, Andrew W.
Wilson, David M.
Wood, Anthony
[J]. NATURE CHEMISTRY, 2018, 10 (04) : 383 - 394
[8] Modern Carbon-Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis
Campbell, Michael G.
Ritter, Tobias
[J]. CHEMICAL REVIEWS, 2015, 115 (02) : 612 - 633
[9] Palladium(II)-Catalyzed Selective Monofluorination of Benzoic Acids Using a Practical Auxiliary: A Weak-Coordination Approach
Chan, Kelvin S. L.
Wasa, Masayuki
Wang, Xisheng
Yu, Jin-Quan
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) : 9081 - 9084
[10] Palladium-Catalyzed ortho-Selective C-H Fluorination of Oxalyl Amide-Protected Benzylamines
Chen, Changpeng
Wang, Chao
Zhang, Jingyu
Zhao, Yingsheng
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (02) : 942 - 949

← 1 2 3 4 5 6 7 →