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Synlett 2023; 34(18): 2193-2196
DOI: 10.1055/a-2158-9726
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Modern Boron Chemistry: 60 Years of the Matteson Reaction

Addition of a Phosphinoboronate Ester to Borole and Borafluorene

Manjur O. Akram
a   Baylor University, Department of Chemistry and Biochemistry, One Bear Place #97348, Waco, TX 76798, USA
,
Christopher M. Vogels
b   Mount Allison University, Department of Chemistry and Biochemistry, Sackville, NB E4L 1E4, Canada
,
Webster L. Santos 
c   Virginia Tech, Department of Chemistry, Blacksburg, VA 24060, USA
,
Stephen A. Westcott
b   Mount Allison University, Department of Chemistry and Biochemistry, Sackville, NB E4L 1E4, Canada
,
Caleb D. Martin∗
a   Baylor University, Department of Chemistry and Biochemistry, One Bear Place #97348, Waco, TX 76798, USA
› InstitutsangabenWe are grateful to the Welch Foundation (Grant No. AA-1846) and the National Science Foundation (Award No. 1753025) for their generous support of this work.
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Dedicated to Professor Donald Matteson and in memory of the late Professor Stephen Westcott in recognition of their contributions to organoboron chemistry.

Abstract

The additions of the phosphinoboronate ester Ph2PBpin to an antiaromatic borole and a borafluorene is reported. The Lewis acid/base adducts are obtained in excellent yields and represent the first P-donor adducts of Ph2PBpin.

Key words

pinacol diphenylphosphinoboronate - boroles - borafluorenes - antiaromaticity - Lewis acid

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2158-9726.
  • Supporting Information


Publikationsverlauf

Eingereicht: 27. Juli 2023

Angenommen nach Revision: 22. August 2023

Accepted Manuscript online:
23. August 2023

Artikel online veröffentlicht:
22. September 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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  • 53 Adducts 1 and 2: General Procedure A solution of PPh2Bpin (0.50 mmol, 156 mg) in benzene (4 mL) was added dropwise to a solution of pentaphenyl-1H-borole or 9-phenyl-9-borafluorene (0.5 mmol) in benzene (4 mL) at rt. The solution instantly became colorless, and the mixture was stirred for 10 min at rt. The solvent was then removed in vacuo and the residue was washed with cold pentane (2 × 5 mL) and dried in vacuo. 1 Pale-yellow powder; yield: 319 mg (84%,); mp 216–219 °C. FTIR (neat): (ranked intensity) 1593 (11), 1483 (8), 1438 (9), 1340 (12), 1245 (5), 1129 (2), 1028 (13), 958 (14), 841 (4), 792 (6), 741 (7), 693 (1), 542 (10), 505 (3), 460 (15) cm–1. 1H NMR (400 MHz, CDCl3): δ = 7.77 (d, J = 6.9 Hz, 2 H), 7.43–7.38 (m, 6 H), 7.33–7.27 (m, 3 H), 7.24–7.22 (m, 4 H), 6.90–6.85 (m, 6 H), 6.82–6.78 (m, 6 H), 6.75–6.74 (m, 4 H), 6.59 (d, J = 7.0 Hz, 4 H), 1.01 (s, 12 H). 13C{1H} NMR (101 MHz, CDCl3): δ = 154.5, 153.5, 153.4, 143.5, 140.5, 135.4 (d, J = 8.5 Hz), 135.2 (d, J = 12.8 Hz), 130.4 (d, J = 2.6 Hz), 130.3 (d, J = 2.6 Hz), 129.7, 127.7, 127.6, 127.3, 126.9, 126.8, 125.9, 125.4, 125.2, 125.0, 124.3, 86.5, 86.5, 24.6. 31P NMR (162 MHz, CDCl3): δ = –34.2. 11B NMR (128 MHz, CDCl3): δ = 30.8, –5.2. HRMS (ESI): the adduct peak was not observed in the HRMS. Anal. Calcd for C52H47B2O2P: C, 82.56; H, 6.26. Found: C 82.36, H 6.32. Single crystals of 1 for X-ray diffraction studies were grown from a CH2Cl2 solution by vapor diffusion into toluene. 2 White powder; yield: 256 mg (93%,); mp 189–191 °C. FTIR (neat): (ranked intensity) 1483 (14), 1435 (8), 1373 (12), 1348 (10), 1244 (6), 1128 (4), 1103 (13), 961 (11), 836 (5), 734 (1), 696 (3), 647 (9), 616 (15), 506 (2), 427 (7) cm–1. 1H NMR (400 MHz, CDCl3): δ = 7.65 (d, J = 7.7 Hz, 4 H), 7.55 (d, J = 7.2 Hz, 2 H), 7.41 (td, J = 7.2, 1.6 Hz, 2 H), 7.30–7.15 (m, 13 H), 7.12 (t, J = 7.2 Hz, 2 H), 1.15 (s, 12 H). 13C{1H} NMR (101 MHz, CDCl3): δ = 153.0, 149.4, 134.6 (d, J = 7.5 Hz), 134.2, 132.9, 130.5 (d, J = 2.6 Hz), 128.3 (d, J = 9.5 Hz), 127.5, 126.5, 126.2, 125.8, 125.6, 125.6, 86.6, 86.6, 24.7. 31P NMR (162 MHz, CDCl3): δ = –35.2. 11B NMR (128 MHz, CDCl3): δ = 30.9, –9.3. HRMS (ESI): m/z [M + H] calcd for C36H36B2O2P: 553.2634; found: 553.2610. Anal. Calcd for C36H35B2O2P: C, 78.29; H, 6.39. Found: C, 78.54; H, 6.55. Single crystals for X-ray diffraction studies were grown from a CH2Cl2 solution of 2 by vapor diffusion into toluene.