Ru-Catalyzed Asymmetric Reductive Amination of Aryl-Trifluoromethyl Ketones for Synthesis of Primary α-(Trifluoromethyl)arylmethylamines

Wang，Yuan Zheng1; Hu，Le’an1; Bai，Shao Tao1,2; Zhang，Xumu1

2023-07-14

10.1021/acs.orglett.3c01734

Organic Letters   Impact Factor & Quartile

1523-7060

1523-7052

The ruthenium-catalyzed asymmetric reductive amination of aryl-trifluoromethyl ketones affording high value primary α-(trifluoromethyl)arylmethylamines using cheap NHOAc as the nitrogen source and H as the reductant is reported. This user-friendly and simple catalytic method tolerates various aromatic functions with electron-withdrawing or -donating substituents at the para- or meta-positions and as well challenging heteroaromatic functions, yielding primary α-(trifluoromethyl)arylmethylamines with excellent chemoselectivities, enantioselectivities, and useful yields (80-97% ee, 51-92% isolated yields). Finally, scalable and concise synthesis of key drug intermediates using this methodology is presented.

SCI ; IC ; CCR

English

NI Journal Papers ; NI论文

First ; Corresponding

Shenzhen High-Caliber Personnel of SZPT[6023330003K] ; National Natural Science Foundation of China[21991113] ; National Key Ramp;D Program of China["2021YFA1500200","2021YFA0910804"] ; Guangdong Guangdong Basic and Applied Basic Research Foundation[2021A1515110808]

Chemistry

Chemistry, Organic

WOS:001018794600001

AMER CHEMICAL SOC

CHEMISTRY

2-s2.0-85164802709

Scopus

1.Department of Chemistry and Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis,Southern University of Science and Technology,Shenzhen,1088 Xueyuan Road,518055,China
2.Institute of Carbon-Neutral Technology and Center for Carbon-Neutrality Catalysis and Engineering,Shenzhen Polytechnic,Shenzhen,No. 7098 Liuxian Avenue, Nanshan District,518055,China

Wang，Yuan Zheng,Hu，Le’an,Bai，Shao Tao,et al. Ru-Catalyzed Asymmetric Reductive Amination of Aryl-Trifluoromethyl Ketones for Synthesis of Primary α-(Trifluoromethyl)arylmethylamines[J]. Organic Letters,2023,25(27):5033-5037.

Wang，Yuan Zheng,Hu，Le’an,Bai，Shao Tao,&Zhang，Xumu.(2023).Ru-Catalyzed Asymmetric Reductive Amination of Aryl-Trifluoromethyl Ketones for Synthesis of Primary α-(Trifluoromethyl)arylmethylamines.Organic Letters,25(27),5033-5037.

Wang，Yuan Zheng,et al."Ru-Catalyzed Asymmetric Reductive Amination of Aryl-Trifluoromethyl Ketones for Synthesis of Primary α-(Trifluoromethyl)arylmethylamines".Organic Letters 25.27(2023):5033-5037.