Enantioselective Synthesis of Axially Chiral 1-Arylisoquinolines by Iridium(I)-Catalyzed Hydroarylation of Alkynes

Qiansujia Zhou; Si-Yong Yin; Dong-Song Zheng; Wen-Wen Zhang; Su-Zhen Zhang; Qing Gu; Shu-Li You

doi:10.1055/a-2021-9514

Synlett, Table of Contents

Synlett 2023; 34(12): 1442-1446
DOI: 10.1055/a-2021-9514

cluster

Special Issue Honoring Masahiro Murakami’s Contributions to Science

Enantioselective Synthesis of Axially Chiral 1-Arylisoquinolines by Iridium(I)-Catalyzed Hydroarylation of Alkynes

Authors

Qiansujia Zhou

^aCollege of Science, University of Shanghai for Science and Technology, Shanghai 200093, P. R. of China

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Si-Yong Yin

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Dong-Song Zheng

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Wen-Wen Zhang

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Su-Zhen Zhang

^aCollege of Science, University of Shanghai for Science and Technology, Shanghai 200093, P. R. of China

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Qing Gu∗

^aCollege of Science, University of Shanghai for Science and Technology, Shanghai 200093, P. R. of China

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Shu-Li You∗

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

Abstract

All articles of this category

Abstract

Ir(I)-catalyzed atroposelective hydroarylation of alkynes with 1-arylisoquinolines through C–H functionalization was realized. In the presence of 5 mol% of [Ir(cod)Cl]₂ and 10 mol% of QUINOX-P, a wide range of axially chiral alkenylated biaryls were obtained in up to 98% yield and 97% ee. Notably, only one equivalent of the alkyne was required to guarantee a high efficiency of this C–H functionalization process. This reaction exhibits excellent functional-group tolerance under mild conditions.

Key words

alkynes - isoquinolines - axial chirality - C–H functionalization - iridium catalysis - asymmetric synthesis

Full Text

References

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14 (S _a,E)-1-[2-(1,2-Bis(4-methoxyphenyl)vinyl]-1-naphthyl)benzo[h]isoquinoline (3aa) Yellow foam; yield: 105.7 mg (97%, 96% ee); [α]_D ²⁴ –394.9 (c = 0.2, CHCl₃). HPLC [Chiralpak AD-H column (4.6 × 250 mm), hexane/i-PrOH (90:10); flow rate: 1.0 mL/min, λ = 254 nm, 25 ℃]. t _R (minor) = 8.23 min; t _R (major) = 23.86 min. IR (ATR): = 2925, 2854, 1605, 1509, 1462, 1291, 1247, 1176, 1033, 853, 826, 752, 669 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 8.57 (d, J = 5.2 Hz, 1 H), 8.01 (d, J = 8.4 Hz, 1 H), 7.95 (d, J = 8.0 Hz, 1 H), 7.83–7.75 (m, 2 H), 7.62 (d, J = 8.4 Hz, 1 H), 7.57 (d, J = 8.8 Hz, 1 H), 7.52–7.46 (m, 2 H), 7.46–7.41 (m, 2 H), 7.38 (d, J = 8.4 Hz, 1 H), 7.28–7.19 (m, 1 H), 7.08–7.00 (m, 1 H), 6.48–6.48 (m, 4 H), 6.27 (d, J = 8.4 Hz, 2 H), 6.16 (s, 1 H), 6.09 (d, J = 8.4 Hz, 2 H), 3.62 (s, 3 H), 3.52 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 158.0, 157.7, 157.1, 143.6, 140.7, 140.2, 139.1, 137.8, 133.5, 133.1, 132.2, 132.1, 131.9, 130.9, 130.6, 130.22, 130.17, 129.6, 129.3, 128.7, 128.4, 128.1, 126.92, 126.90, 126.86, 126.6, 126.4, 126.3, 126.0, 125.5, 120.9, 113.1, 112.8, 55.1, 55.0. HRMS (ESI-TOF): m/z [M + H]⁺ calcd for C₃₉H₃₀NO₂: 544.2271; found: 544.2265.
15 Xie J.-H, Wang L.-X, Fu Y, Zhu S.-F, Fan B.-M, Duan H.-F, Zhou Q.-L. J. Am. Chem. Soc. 2003; 125: 4404
16 Imamoto T, Sugita K, Yoshida K. J. Am. Chem. Soc. 2005; 127: 11934
17 1-(2-[1,2-Diarylvinyl]-1-naphthyl)benzo[h]isoquinolines 3: General Procedure Under an argon atmosphere, a flame-dried 10 mL Schlenk tube was charged with [Ir(cod)Cl]₂ (6.7 mg, 0.01 mmol, 5 mol%), (S,S)-QUINOX-P (6.6 mg, 0.02 mmol, 10 mol%) and anhyd THF (1.0 mL), and the resulting solution was stirred for 10 min at rt. Then, isoquinoline 1 (0.2 mmol), alkyne 2 (0.2 mmol), and NaBAr^F (35.4 mg, 0.04 mmol, 20 mol%) were added under argon and the tube was heated at 80 °C for 10–24 h. The mixture was then cooled to rt and the crude product was purified by preparative TLC (PE–EtOAc, 5:1).

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