Palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates at the C–Cl site
Chen, Zicong; Gu, Changxue; Yuen, On Ying; So, Chau Ming; Chemical Science  (2022) –; doi:10.1039/D1SC06701J

data_1566618
_publ_section_title
;
 Palladium-catalyzed chemoselective direct \a-arylation of carbonyl
 compounds with chloroaryl triflates at the C--Cl site
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC06701J
_journal_year                    2022
_chemical_formula_moiety         'C35 H48 N P'
_chemical_formula_sum            'C35 H48 N P'
_chemical_formula_weight         513.71
_chemical_name_systematic        PAdSelectPhos
_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             2019-06-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-10-21 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                96.831(6)
_cell_angle_beta                 101.037(6)
_cell_angle_gamma                111.157(7)
_cell_formula_units_Z            2
_cell_length_a                   10.6770(8)
_cell_length_b                   11.8045(10)
_cell_length_c                   12.4452(9)
_cell_measurement_reflns_used    3277
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6670
_cell_measurement_theta_min      3.0070
_cell_volume                     1405.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -14.00  30.00   1.00    5.00    --   15.49  19.00  30.00   44
  2  \w     51.00  86.00   1.00    5.00    --   15.49  19.00  30.00   35
  3  \w     40.00  66.00   1.00    5.00    --   15.49  57.00  90.00   26
  4  \w     -3.00  85.00   1.00    5.00    --   15.49  38.00 -90.00   88
  5  \w    -23.00  32.00   1.00    5.00    --   15.49 -57.00 120.00   55
  6  \w    -25.00  54.00   1.00    5.00    --   15.49 -99.00  90.00   79
  7  \w    -25.00  22.00   1.00    5.00    --  -16.28 -99.00 -60.00   47
  8  \w     36.00  62.00   1.00    5.00    --   15.49 178.00  60.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0236709000
_diffrn_orient_matrix_UB_12      0.0408939000
_diffrn_orient_matrix_UB_13      -0.0269012000
_diffrn_orient_matrix_UB_21      0.0636974000
_diffrn_orient_matrix_UB_22      0.0250928000
_diffrn_orient_matrix_UB_23      -0.0151855000
_diffrn_orient_matrix_UB_31      -0.0283538000
_diffrn_orient_matrix_UB_32      -0.0450796000
_diffrn_orient_matrix_UB_33      -0.0506575000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11455
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.702
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.214
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0422P)^2^+0.4038P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1127
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4338
_reflns_number_total             5514
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06701j2.cif
_cod_data_source_block           exp_6910
_cod_database_code               1566618
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.964
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C13(H13), C29(H29), C18(H18), C15(H15), C5(H5), C3(H3), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C2(H2A,H2B), C17(H17A,H17B), C16(H16A,H16B), C6(H6A,H6B),
 C19(H19A,H19B), C9(H9A,H9B), C34(H34A,H34B), C20(H20A,H20B), C4(H4A,H4B),
 C14(H14A,H14B), C30(H30A,H30B), C31(H31A,H31B), C33(H33A,H33B), C32(H32A,H32B),
  C10(H10A,H10B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C26(H26), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C)
;
_shelx_res_checksum              67124
_shelx_hkl_checksum              73692
_olex2_date_sample_data_collection 2019-06-10
_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 1.227
_oxdiff_exptl_absorpt_empirical_full_min 0.780