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单齿瞬态导向基团辅助的钯催化苯甲醛与芳烃直接脱氢交叉偶联制备9-芴酮

Monodentate Transient Directing Group Assisted Pd-Catalyzed Direct Dehydrogenative Cross-Coupling of Benzaldehydes with Arenes toward 9-Fluorenones.

作者信息

Wang Yi-Feng, Xu Wen-Gang, Sun Bing, Yu Qin-Qin, Li Tuan-Jie, Zhang Fang-Lin

机构信息

School of Chemistry, Chemical Engineering and Life Sciences , Wuhan University of Technology , Wuhan 430070 , P.R. China.

School of Chemistry & Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials , Jiangsu Normal University , Xuzhou 221116 , P.R. China.

出版信息

J Org Chem. 2019 Oct 18;84(20):13104-13111. doi: 10.1021/acs.joc.9b02139. Epub 2019 Sep 19.

DOI:10.1021/acs.joc.9b02139
PMID:31497964
Abstract

Commercially available 3,5-bis(trifluoromethyl)aniline was found to be a highly efficient monodentate transient directing group (MonoTDG) for the palladium-catalyzed direct dehydrogenative cross-coupling of benzaldehydes with arenes. A diverse set of symmetrical and unsymmetrical 9-fluorenones was readily obtained in yields of 32-72% along with excellent regioselectivities and broad functional group compatibility as well as high atom economy under mild conditions via a dual carbon-hydrogen (C-H) bond activation sequence.

摘要

已发现市售的3,5-双(三氟甲基)苯胺是用于钯催化苯甲醛与芳烃直接脱氢交叉偶联的高效单齿瞬态导向基团(MonoTDG)。通过双碳-氢键(C-H)活化序列,在温和条件下,可轻松获得各种对称和不对称的9-芴酮,产率为32-72%,同时具有出色的区域选择性、广泛的官能团兼容性以及高原子经济性。

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