Enantioselective copper-catalyzed hydrophosphination of alkenyl isoquinolines

Yang, Qingjing; Zhou, Jian; Wang, Jun

doi:10.1039/d2sc06950d

Cited by 21 publications

(17 citation statements)

References 70 publications

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“…NMR Spectra were recorded on a Bruker DPX-500 (400) spectrometer at 500 MHz or 400 MHz for 1 H NMR, 160 MHz for 31 P NMR and 100 MHz or 125 MHz for 13 C NMR in CDCl3 with tetramethylsilane (TMS) or the residual deuterated solvent peaks as internal standard. Chemical shifts (δ) are reported in ppm, and coupling constants (J) are in Hertz (Hz).…”

Section: Synthesis Papermentioning

confidence: 99%

“…1-bromonaphthalen-2-yl 3-methylbenzoate (2d) 13 C NMR (100 MHz, CDCl3) δ 164. 7, 146.7, 138.6, 134.8, 132.8, 132.5, 131.0, 129.0, 128.9, 128.6, 128.3, 127.9, 127.7, 127.1, 126.4, 122.1, 115.3, 21.4.…”

Section: Synthesis Papermentioning

confidence: 99%

“…3, 146.6, 133.9, 133.5, 133.2, 132.8, 132.7, 131.9, 129.8, 129.3, 129.2, 129.0, 128.3, 128.2, 128.2, 128.2, 128.1, 126.7, 126.4, 126.2, 126.2, 125.9, 125.7, 125.4, 121.8 ). 13 C NMR (100 MHz, CDCl3) δ 176. 8, 146.7, 133.9, 133.6, 133.0, 132.8, 131.75, 129.1, 128.9, 128.3, 128.1, 128.0, 128.0, 126.5, 126.3, 126.2, 126.1, 125.9, 125.5, 125.2, 121.8, 38.6, 26.4 13 C NMR (100 MHz, CDCl3) δ 165.3, 1467, 144.0, 133.9, 133.5, 132.9, 132.7, 131.8, 129.8, 129.3, 129.0, 129.0, 128.3, 128.2, 128.2, 128.1, 126.6, 126.5, 126.4, 126.2, 126.2, 125.8, 125.7, 125.4, 122.0, 21.7 13 C NMR (100 MHz, CDCl3) δ 165.…”

Section: Synthesis Papermentioning

confidence: 99%

“…13 C NMR (100 MHz, CDCl3) δ 176. 8, 146.7, 133.9, 133.6, 133.0, 132.8, 131.75, 129.1, 128.9, 128.3, 128.1, 128.0, 128.0, 126.5, 126.3, 126.2, 126.1, 125.9, 125.5, 125.2, 121.8, 38.6, 26.4 13 C NMR (100 MHz, CDCl3) δ 165.3, 1467, 144.0, 133.9, 133.5, 132.9, 132.7, 131.8, 129.8, 129.3, 129.0, 129.0, 128.3, 128.2, 128.2, 128.1, 126.6, 126.5, 126.4, 126.2, 126.2, 125.8, 125.7, 125.4, 122.0, 21.7 13 C NMR (100 MHz, CDCl3) δ 165. 5, 146.7, 138.0, 133.9, 133.9, 133.6, 132.9, 132.7, 131.9, 130.3, 129.3, 129.2, 129.0, 128.4, 128.2, 128.2, 128.1, 128.1, 126.9, 126.7, 126.4, 126.2, 126.2, 125.9, 125.7, 125.4, 121.8, 21 7, 140.4, 134.0, 133.6, 133.1, 132.8, 132.2, 131.8, 131.4, 130.6, 129.3, 129.1, 128.7, 128.3, 128.3, 128.2, 128.1, 126.7, 126.5, 126.3, 126.0, 125.7, 125.5, 125.4, 122.1, 21 7.42 (m, 9H), 7.36 -7.31 (m, 2H), 7.18 -7.12 (m, 2H).…”

Section: Synthesis Papermentioning

confidence: 99%

“…5, 146.7, 138.0, 133.9, 133.9, 133.6, 132.9, 132.7, 131.9, 130.3, 129.3, 129.2, 129.0, 128.4, 128.2, 128.2, 128.1, 128.1, 126.9, 126.7, 126.4, 126.2, 126.2, 125.9, 125.7, 125.4, 121.8, 21 7, 140.4, 134.0, 133.6, 133.1, 132.8, 132.2, 131.8, 131.4, 130.6, 129.3, 129.1, 128.7, 128.3, 128.3, 128.2, 128.1, 126.7, 126.5, 126.3, 126.0, 125.7, 125.5, 125.4, 122.1, 21 7.42 (m, 9H), 7.36 -7.31 (m, 2H), 7.18 -7.12 (m, 2H). 13 C NMR (100 MHz, CDCl3) δ 164. 4, 146.5, 139.7, 133.9, 133.6, 132.8, 132.6, 131.9, 131.9, 131.1, 129.4, 129.2, 129.0, 128.6, 128.3, 128.2, 128.1, 126.7, 126.4, 126.3, 126.1, 125.9, 125.8, 125.3, 121.6.…”

Section: Synthesis Papermentioning

confidence: 99%

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Herein, we report a manganese‐catalyzed three‐component vinylation strategy for the synthesis of vinylphosphines from readily available alcohols, sulfones, and phosphines via acceptorless dehydrogenative strategy. This multi‐component, four‐stage, one‐pot protocol offers a stereoselective approach, overcoming the challenges associated with achieving these products through the hydrophosphination of terminal alkynes. The reaction utilizes sulfones and common alcohols to access both (E)‐β‐substituted vinylphosphines (using methanol) and α‐substituted vinylphosphines (using primary alcohols) in yields ranging from 52% to 99%, with E:Z stereoselectivity of 95:5 to 99:1. Importantly, the synthesized branched‐substituted vinylphosphines exhibited superior ligand performance in the copper‐catalyzed cross‐coupling of aryl bromides with pyrazole compared to the commercially available PPh3 and diphenyl(vinyl)phosphane.

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Chiral 1, n‐bis(boronate) plays a crucial role in organic synthesis and medicinal chemistry. However, their catalytic and asymmetric synthesis has long posed a challenge in terms of operability and accessibility from readily available substrates. The recent discovery of the C═C bond formation through β‐C elimination of methylenecyclopropanes (MCP) has provided an exciting opportunity to enhance molecular complexity. In this study, the catalyzed asymmetric cascade hydroboration of MCP is developed. By employing different ligands, various homoallylic boronate intermediate are obtained through the hydroboration ring opening process. Subsequently, the cascade hydroboration with HBpin or B2pin2 resulted in the synthesis of enantioenriched chiral 1,3‐ and 1,4‐bis(boronates) in high yields, accompanied by excellent chemo‐ and enantioselectivities. The selective transformation of these two distinct C─B bonds also demonstrated their application potential in organic synthesis.

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Enantioselective copper-catalyzed hydrophosphination of alkenyl isoquinolines

Abstract: An enantioselective hydrophosphination of alkenyl isoquinolines is developed by using copper-chiral diphosphine ligand catalyst. It provides a direct and atom-efficient approach to prepare a variety of chiral phosphines with isoquinoline...

Cited by 21 publications

References 70 publications

Palladium/Azaphos-Catalyzed Asymmetric Suzuki–Miyaura Coupling

Palladium/Azaphos-Catalyzed Asymmetric Suzuki–Miyaura Coupling

Manganese‐Catalyzed Three‐Component Vinylation of Phosphines with Sulfones and Alcohols

Enantio‐ and Regioselective Cascade Hydroboration of Methylenecyclopropanes for Facile Access to Chiral 1,3‐ and 1,4‐Bis(boronates)

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