A phosphine free, inorganic base free, one-pot tandem Mizoroki–Heck olefination/direct arylation/hydrogenation sequence, to give multicyclic alkylated heteroarenes
Kehoe, Roberta A.; Light, Mark E.; Jones, David J.; McGlacken, Gerard P.; Green Chemistry 25 (2023) 5654–5660; doi:10.1039/D3GC01403G

data_7246952
_publ_section_title
;
 A phosphine free, inorganic base free, one-pot tandem Mizoroki--Heck
 olefination/direct arylation/hydrogenation sequence, to give multicyclic
 alkylated heteroarenes
;
_journal_issue                   14
_journal_name_full               'Green Chemistry'
_journal_page_first              5654
_journal_page_last               5660
_journal_paper_doi               10.1039/D3GC01403G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C20 H16 O'
_chemical_formula_sum            'C20 H16 O'
_chemical_formula_weight         272.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-01
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_audit_update_record
;
2022-09-01 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                84.533(7)
_cell_angle_beta                 89.069(7)
_cell_angle_gamma                74.931(6)
_cell_formula_units_Z            2
_cell_length_a                   6.3822(4)
_cell_length_b                   10.2110(8)
_cell_length_c                   11.3886(12)
_cell_measurement_reflns_used    2600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.7330
_cell_measurement_theta_min      3.8850
_cell_volume                     713.37(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_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    -73.00 -18.00   0.50    1.00    --  -44.84 124.00 111.00  110
  2  \w     10.00  46.00   0.50    1.00    --   44.84-124.00  32.00   72
  3  \w     50.00  77.00   0.50    1.00    --   44.84-124.00  32.00   54
  4  \w    -98.00 -72.00   0.50    5.00    --  -97.00 124.00 111.00   52
  5  \w    -63.00 -31.00   0.50    5.00    --  -97.00 124.00 111.00   64
  6  \w     89.00 142.00   0.50    5.00    --  109.75 124.00 111.00  106
  7  \w    -22.00  29.00   0.50    1.00    --  -44.84  38.00 -60.00  102
  8  \w    -28.00  12.00   0.50    1.00    --   44.84 -38.00  90.00   80
  9  \w     39.00  74.00   0.50    1.00    --   44.84  38.00 150.00   70
 10  \w     39.00  64.00   0.50    1.00    --   44.84 -77.00-150.00   50
 11  \w    -23.00  12.00   0.50    1.00    --   44.84 -77.00-150.00   70
 12  \w    -30.00  13.00   0.50    1.00    --   44.84 -38.00 120.00   86
 13  \w    -19.00  13.00   0.50    1.00    --   44.84 -38.00  30.00   64
 14  \w    -27.00   9.00   0.50    1.00    --   44.84 -38.00 -30.00   72
 15  \w    -49.00 -23.00   0.50    5.00    --  -97.00  61.00  90.00   52
 16  \w   -168.00-142.00   0.50    5.00    --  -97.00 -30.00  90.00   52
 17  \w    -92.00 -65.00   0.50    5.00    --  -97.00  99.00  69.90   54
 18  \w    -51.00 -25.00   0.50    5.00    --  -97.00  99.00  69.90   52
 19  \w   -138.00 -92.00   0.50    5.00    --  -97.00 -15.00-180.00   92
 20  \w    -93.00 -65.00   0.50    5.00    --  -97.00  93.00-142.12   56
 21  \w    -92.00 -37.00   0.50    5.00    --  -97.00  96.00 -50.71  110
 22  \w    -92.00 -23.00   0.50    5.00    --  -97.00  90.00 134.20  138
 23  \w   -138.00 -90.00   0.50    5.00    --  -97.00 -30.00  90.00   96
 24  \w   -155.00-130.00   0.50    5.00    --  -97.00-124.00  32.00   50
 25  \w    105.00 155.00   0.50    5.00    --  109.75  30.00  30.00  100
 26  \w     41.00  71.00   0.50    5.00    --  109.75 -77.00  90.00   60
 27  \w     37.00  65.00   0.50    5.00    --  109.75 -77.00-180.00   56
 28  \w    106.00 131.00   0.50    5.00    --  109.75  15.00 -60.00   50
 29  \w     39.00  67.00   0.50    5.00    --  109.75 -77.00-120.00   56
 30  \w    105.00 130.00   0.50    5.00    --  109.75  15.00   0.00   50
 31  \w     41.00  69.00   0.50    5.00    --  109.75 -77.00  30.00   56
 32  \w     37.00  71.00   0.50    5.00    --  109.75 -77.00 -60.00   68
 33  \w    104.00 129.00   0.50    5.00    --  109.75  15.00  90.00   50
 34  \w     39.00  68.00   0.50    5.00    --  109.75 -77.00 120.00   58
 35  \w     39.00  88.00   0.50    5.00    --  109.75 -95.00  30.00   98
 36  \w    104.00 129.00   0.50    5.00    --  109.75  15.00  30.00   50
 37  \w     63.00  93.00   0.50    5.00    --  109.75 -95.00   0.00   60
 38  \w     41.00  71.00   0.50    5.00    --  109.75 -77.00-150.00   60
 39  \w    104.00 129.00   0.50    5.00    --  109.75  15.00-180.00   50
 40  \w     69.00  95.00   0.50    5.00    --  109.75-125.00 -30.00   52
 41  \w     57.00  91.00   0.50    5.00    --  109.75 -95.00 -90.00   68
 42  \w     52.00  78.00   0.50    5.00    --  109.75 -95.00  90.00   52
 43  \w    109.00 151.00   0.50    5.00    --  109.75  30.00-120.00   84
 44  \w    104.00 129.00   0.50    5.00    --  109.75  15.00 -30.00   50
 45  \w    114.00 158.00   0.50    5.00    --  109.75  30.00 -60.00   88
 46  \w     68.00  94.00   0.50    5.00    --  109.75-124.00  32.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0247354000
_diffrn_orient_matrix_UB_12      0.1430337000
_diffrn_orient_matrix_UB_13      -0.0422820000
_diffrn_orient_matrix_UB_21      -0.0331476000
_diffrn_orient_matrix_UB_22      -0.0259462000
_diffrn_orient_matrix_UB_23      -0.1286079000
_diffrn_orient_matrix_UB_31      -0.2465464000
_diffrn_orient_matrix_UB_32      0.0591587000
_diffrn_orient_matrix_UB_33      0.0118277000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5814
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        66.473
_diffrn_reflns_theta_max         66.473
_diffrn_reflns_theta_min         3.899
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.1453
_refine_ls_R_factor_gt           0.1351
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0852P)^2^+9.0160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3868
_refine_ls_wR_factor_ref         0.3906
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2067
_reflns_number_total             2417
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc01403g2.cif
_cod_data_source_block           2022acc0021_d1_100k
_cod_depositor_comments
'Adding full bibliography for 7246950--7246958.cif.'
_cod_database_code               7246952
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C12H12O1
_chemical_oxdiff_usercomment     RAK-437
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.901
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              92870
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id RAK-437
_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 1.738
_oxdiff_exptl_absorpt_empirical_full_min 0.499