Chiral Phosphoric Acid-Catalyzed Remote Control of Axial Chirality at Boron-Carbon Bond

Yang, Junxian1,2,3; Zhang, Ji-Wei; Bao, Wen; Qiu, Sheng-Qi3; Li, Shaoyu1,2; Xiang, Shao-Hua1,2; Song, Jun3; Zhang, Junmin3; Tan, Bin1

2021-08-25

10.1021/jacs.1c05079

Journal of the American Chemical Society   影响因子和分区

0002-7863

1520-5126

The previously elusive catalytic enantioselective construction of axially chiral B-aryl-1,2-azaborines with a C-B stereogenic axis has been realized through a chiral phosphoric acid-catalyzed desymmetrization strategy reported herein. The electrophilic aromatic substitution reaction of 3,5-disubsituted phenols with diazodicarboxamides could afford these axially chiral structures in good efficiency with excellent enantiocontrol. The efficient long-range stereochemical control is achieved by multiple well-defined H-bonding interactions between chiral phosphoric acid and both substrates. Meanwhile, the reaction duration could be markedly shortened with weakly acidic N-H in 1,2-azaborine acting as H-bond donor. The scalability of the reaction and facile cleavage of the N-N bond in the product further demonstrated the practicality of this method.

SCI ; EI ; IC ; CCR

英语

NI论文

第一 ; 通讯

National Natural Science Foundation of China[21825105] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; Guangdong Innovative Program[2019BT02Y335] ; Shenzhen Special Funds["JCYJ20180305123508258",20200812202943001] ; Shenzhen Nobel Prize Scientists Laboratory Project[C17213101] ; Principal Foundation of Shenzhen University[8570700000307] ; Project of Department of Education of Guangdong Province[2020KTSCX116] ; SUSTech Special Fund for the Construction of High-Level Universities[G02216402]

Chemistry

Chemistry, Multidisciplinary

WOS:000691789500004

AMER CHEMICAL SOC

20213610849168

Boron ; Carbon ; Catalysis ; Remote control ; Substitution reactions

Nonferrous Metals and Alloys excluding Alkali and Alkaline Earth Metals:549.3 ; Control Systems:731.1 ; Chemical Reactions:802.2 ; Chemical Products Generally:804 ; Inorganic Compounds:804.2

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
2.Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen 518055, Peoples R China
3.Shenzhen Univ, Coll Phys & Optoelect Engn, Coll Chem & Environm Engn, Int Joint Res Ctr Mol Sci, Shenzhen 518060, Peoples R China

Yang, Junxian,Zhang, Ji-Wei,Bao, Wen,et al. Chiral Phosphoric Acid-Catalyzed Remote Control of Axial Chirality at Boron-Carbon Bond[J]. Journal of the American Chemical Society,2021,143(33):12924-12929.

Yang, Junxian.,Zhang, Ji-Wei.,Bao, Wen.,Qiu, Sheng-Qi.,Li, Shaoyu.,...&Tan, Bin.(2021).Chiral Phosphoric Acid-Catalyzed Remote Control of Axial Chirality at Boron-Carbon Bond.Journal of the American Chemical Society,143(33),12924-12929.

Yang, Junxian,et al."Chiral Phosphoric Acid-Catalyzed Remote Control of Axial Chirality at Boron-Carbon Bond".Journal of the American Chemical Society 143.33(2021):12924-12929.