Synthesis of 3-propargyl isoindolinones by Pd/Cu-catalyzed enantioselective Heck/Sonogashira reaction of enamides.
Wang, Qiang; Pan, Ya-Lin; Liang, Ren-Xiao; Hu, Yuan-Yuan; Jia, Yi-Xia; Organic & biomolecular chemistry 23 (2025) 1073–1077; doi:10.1039/d4ob01881h

data_7160322
_publ_section_title
;
 Synthesis of 3-propargyl isoindolinones by Pd/Cu-catalyzed
 enantioselective Heck/Sonogashira reaction of enamides.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1073
_journal_page_last               1077
_journal_paper_doi               10.1039/d4ob01881h
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H17 N O'
_chemical_formula_sum            'C19 H17 N O'
_chemical_formula_weight         275.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-07-08 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.16669(7)
_cell_length_b                   13.97128(11)
_cell_length_c                   14.98548(11)
_cell_measurement_reflns_used    23040
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1060
_cell_measurement_theta_min      4.3050
_cell_volume                     1500.46(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     63.00  89.00   1.00    1.00    --    0.00  38.00-150.00   26
  2  \w    -18.00   8.00   1.00    1.00    --    0.00  38.00-150.00   26
  3  \w    -87.00  18.00   1.00    1.00    --    0.00 -38.00 -30.00  105
  4  \w    -29.00  35.00   1.00    1.00    --    0.00  82.00  30.00   64
  5  \w    -88.00  -1.00   1.00    1.00    --    0.00 -77.00 120.00   87
  6  \w    -28.00  17.00   1.00    1.00    --    0.00 -38.00  30.00   45
  7  \w     51.00  83.00   1.00    1.00    --    0.00  77.00 120.00   32
  8  \w     49.00  81.00   1.00    1.00    --    0.00  38.00 -90.00   32
  9  \w    -89.00 -63.00   1.00    1.00    --    0.00 -38.00  30.00   26
 10  \w     55.00  82.00   1.00    1.00    --    0.00  82.00  30.00   27
 11  \w    -30.00  34.00   1.00    1.00    --    0.00  77.00 120.00   64
 12  \w    -19.00  12.00   1.00    1.00    --    0.00  38.00 -90.00   31
 13  \w    151.00 181.00   1.00    1.00    --   95.80  82.00  30.00   30
 14  \w     64.00  89.00   1.00    1.00    --   95.80  82.00  30.00   25
 15  \w     70.00 100.00   1.00    1.00    --   95.80  64.00 134.14   30
 16  \w    123.00 175.00   1.00    1.00    --   95.80  77.00 -60.00   52
 17  \w     61.00 127.00   1.00    1.00    --   95.80 -82.00-180.00   66
 18  \w    128.00 169.00   1.00    1.00    --   95.80  76.00 165.89   41
 19  \w     65.00  94.00   1.00    1.00    --   95.80  78.00 -37.94   29
 20  \w     78.00 185.00   1.00    1.00    --   95.80  45.00 -90.00  107
 21  \w    110.00 185.00   1.00    1.00    --   95.80  82.00 -30.00   75
 22  \w    157.00 185.00   1.00    1.00    --   95.80  79.00-112.23   28
 23  \w     65.00  91.00   1.00    1.00    --   95.80  82.00   0.00   26
 24  \w     65.00  92.00   1.00    1.00    --   95.80  77.00 -60.00   27
 25  \w     75.00 122.00   1.00    1.00    --   95.80  45.00  90.00   47
 26  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 150.00   26
 27  \w     43.00  78.00   1.00    1.00    --   95.80 -82.00  90.00   35
 28  \w     83.00 125.00   1.00    1.00    --   95.80 -82.00  90.00   42
 29  \w     74.00 132.00   1.00    1.00    --   95.80  61.00  90.00   58
 30  \w    157.00 185.00   1.00    1.00    --   95.80  61.00  90.00   28
 31  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -30.00   26
 32  \w     63.00 185.00   1.00    1.00    --   95.80  82.00-180.00  122
 33  \w     64.00  94.00   1.00    1.00    --   95.80  79.00-112.23   30
 34  \w     65.00 114.00   1.00    1.00    --   95.80  76.00 165.89   49
 35  \w     83.00 108.00   1.00    1.00    --   95.80 -82.00-120.00   25
 36  \w     32.00  69.00   1.00    1.00    --   95.80 -82.00-120.00   37
 37  \w    156.00 183.00   1.00    1.00    --   95.80  77.00  60.00   27
 38  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 39  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 40  \w    129.00 155.00   1.00    1.00    --   95.80  77.00   0.00   26
 41  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  60.00   26
 42  \w     66.00  92.00   1.00    1.00    --   95.80  77.00-180.00   26
 43  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-150.00   26
 44  \w     44.00 106.00   1.00    1.00    --   95.80 -82.00 -30.00   62
 45  \w     76.00 108.00   1.00    1.00    --   95.80  45.00   0.00   32
 46  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 47  \w     67.00  97.00   1.00    1.00    --   95.80  73.00  89.14   30
 48  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  60.00   26
 49  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 50  \w     75.00 135.00   1.00    1.00    --   95.80  45.00-180.00   60
 51  \w     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 52  \w    154.00 182.00   1.00    1.00    --   95.80  45.00  90.00   28
 53  \w     73.00  99.00   1.00    1.00    --   95.80  61.00-120.00   26
 54  \w     76.00 114.00   1.00    1.00    --   95.80  30.00-180.00   38
 55  \w     79.00 109.00   1.00    1.00    --   95.80  30.00  90.00   30
 56  \w    128.00 178.00   1.00    1.00    --   95.80  30.00  90.00   50
 57  \w     75.00 101.00   1.00    1.00    --   95.80  45.00  60.00   26
 58  \w    126.00 182.00   1.00    1.00    --   95.80  45.00  60.00   56
 59  \w     72.00  97.00   1.00    1.00    --   95.80  61.00 -60.00   25
 60  \w     71.00  97.00   1.00    1.00    --   95.80  61.00   0.00   26
 61  \w    129.00 182.00   1.00    1.00    --   95.80  61.00   0.00   53
 62  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 63  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -90.00   25
 64  \w    118.00 171.00   1.00    1.00    --   95.80  77.00-120.00   53
 65  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 66  \w     54.00 124.00   1.00    1.00    --   95.80 -82.00  30.00   70
 67  \w    138.00 164.00   1.00    1.00    --   95.80  64.00 134.14   26
 68  \w     75.00 134.00   1.00    1.00    --   95.80  45.00 -60.00   59
 69  \w     75.00 126.00   1.00    1.00    --   95.80  45.00  30.00   51
 70  \w     75.00 100.00   1.00    1.00    --   95.80  45.00 150.00   25
 71  \w    115.00 168.00   1.00    1.00    --   95.80  78.00 -37.94   53
 72  \w    119.00 163.00   1.00    1.00    --   95.80  45.00-122.88   44
 73  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 74  \w    130.00 181.00   1.00    1.00    --   95.80  82.00 120.00   51
 75  \w     75.00 101.00   1.00    1.00    --   95.80  45.00-122.88   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0346524000
_diffrn_orient_matrix_UB_12      -0.0789787000
_diffrn_orient_matrix_UB_13      -0.0696664000
_diffrn_orient_matrix_UB_21      0.0368785000
_diffrn_orient_matrix_UB_22      -0.0768892000
_diffrn_orient_matrix_UB_23      0.0715545000
_diffrn_orient_matrix_UB_31      -0.2090701000
_diffrn_orient_matrix_UB_32      -0.0004511000
_diffrn_orient_matrix_UB_33      0.0242596000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33187
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.059
_diffrn_reflns_theta_max         67.059
_diffrn_reflns_theta_min         4.327
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1096 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.2671P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0688
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2641
_reflns_number_total             2678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01881h2.cif
_cod_data_source_block           exp_1155
_cod_depositor_comments          'Adding full bibliography for 7160322.cif.'
_cod_database_code               7160322
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.867
_shelx_estimated_absorpt_t_min   0.821
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.172
_oxdiff_exptl_absorpt_empirical_full_min 0.504