Ni-catalyzed arylation of alkynes with organoboronic acids and aldehydes to access stereodefined allylic alcohols.
Tao, Si-Chen; Meng, Fan-Cheng; Wang, Tie; Zheng, Yan-Long; Chemical science 14 (2023) 2040–2045; doi:10.1039/d2sc05894d

data_1568308
_publ_section_title
;
 Ni-catalyzed arylation of alkynes with organoboronic acids and aldehydes
 to access stereodefined allylic alcohols.
;
_journal_issue                   8
_journal_name_full               'Chemical science'
_journal_page_first              2040
_journal_page_last               2045
_journal_paper_doi               10.1039/d2sc05894d
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C24 H30 O4'
_chemical_formula_sum            'C24 H30 O4'
_chemical_formula_weight         382.48
_chemical_name_systematic        1
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc2d4w0g
_audit_creation_date             2022-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-09-24 deposited with the CCDC.	2023-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.264(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.9821(4)
_cell_length_b                   14.8327(3)
_cell_length_c                   19.0411(4)
_cell_measurement_reflns_used    21069
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.9240
_cell_measurement_theta_min      2.3210
_cell_volume                     4501.35(17)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_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     26.00  72.00   0.50    0.50    --   42.30 -54.00 -60.00   92
  2  \w    -35.00  -6.00   0.50    0.50    --   42.30 -82.00  90.00   58
  3  \w    -47.00  22.00   0.50    0.50    --   42.30 -54.00 -60.00  138
  4  \w    100.00 126.00   0.50    0.50    --   42.30  54.00  90.00   52
  5  \w     21.00  70.00   0.50    0.50    --   42.30 -82.00  90.00   98
  6  \w    -47.00  21.00   0.50    0.50    --   42.30 -77.00-120.00  136
  7  \w      5.00  34.00   0.50    0.50    --   42.30 -77.00 120.00   58
  8  \w    -44.00  68.00   0.50    0.50    --   42.30 -54.00 150.00  224
  9  \w     19.00  47.00   0.50    0.50    --   42.30  54.00  90.00   56
 10  \w    -40.00 -14.00   0.50    0.50    --   42.30 -82.00-150.00   52
 11  \w    -16.00  66.00   0.50    0.50    --   42.30 -65.00 -60.00  164
 12  \w    -36.00 -10.00   0.50    0.50    --   42.30 -82.00  30.00   52
 13  \w     77.00 102.00   0.50    0.50    --   42.30  77.00-180.00   50
 14  \w     28.00  53.00   0.50    0.50    --   42.30  77.00-180.00   50
 15  \w     29.00  70.00   0.50    0.50    --   42.30 -82.00 -84.05   82
 16  \w    -43.00   8.00   0.50    0.50    --   42.30 -82.00 -84.05  102
 17  \w    -47.00   1.00   0.50    0.50    --   42.30 -77.00 120.00   96
 18  \w     30.00  67.00   0.50    0.50    --   42.30 -82.00  60.00   74
 19  \w     51.00  94.00   0.50    0.50    --   42.30  54.00  90.00   86
 20  \w    -36.00  19.00   0.50    0.50    --   42.30 -77.00-180.00  110
 21  \w     37.00  65.00   0.50    0.50    --   42.30 -77.00-180.00   56
 22  \w     41.00  70.00   0.50    0.50    --   42.30 -82.00-150.00   58
 23  \w     18.00  43.00   0.50    0.50    --   42.30  43.00 120.00   50
 24  \w     41.00  66.00   0.50    0.50    --   42.30 -65.00-180.00   50
 25  \w     53.00  78.00   0.50    0.50    --   42.30  43.00 120.00   50
 26  \w     36.00  67.00   0.50    0.50    --   42.30 -82.00  30.00   62
 27  \w     36.00  61.00   0.50    0.50    --   42.30 -77.00 120.00   50
 28  \w     35.00  99.00   0.50    1.50    --   93.70 -82.00 120.00  128
 29  \w     13.00 118.00   0.50    1.50    --   93.70 -82.00   0.00  210
 30  \w    119.00 160.00   0.50    1.50    --   93.70  33.00 120.00   82
 31  \w     71.00  97.00   0.50    1.50    --   93.70 -82.00  69.96   52
 32  \w     64.00  90.00   0.50    1.50    --   93.70 -82.00  60.00   52
 33  \w     76.00 105.00   0.50    1.50    --   93.70  68.00-120.00   58
 34  \w      5.00 183.00   0.50    1.50    --   93.70  -8.00 120.00  356
 35  \w     20.00  63.00   0.50    1.50    --   93.70 -82.00 -30.00   86
 36  \w      4.00  33.00   0.50    1.50    --   93.70 -82.00  69.96   58
 37  \w     14.00  74.00   0.50    1.50    --   93.70 -82.00  26.60  120
 38  \w     12.00  95.00   0.50    1.50    --   93.70 -82.00 150.00  166
 39  \w     75.00 102.00   0.50    1.50    --   93.70 -82.00-120.00   54
 40  \w      8.00  98.00   0.50    1.50    --   93.70 -82.00 -90.00  180
 41  \w      4.00  92.00   0.50    1.50    --   93.70 -59.00  30.00  176
 42  \w    100.00 128.00   0.50    1.50    --   93.70 -33.00  60.00   56
 43  \w     77.00 102.00   0.50    1.50    --   93.70 -82.00  76.17   50
 44  \w    120.00 183.00   0.50    1.50    --   93.70  68.00-150.00  126
 45  \w     81.00 115.00   0.50    1.50    --   93.70  68.00-150.00   68
 46  \w     27.00 101.00   0.50    1.50    --   93.70 -82.00 -60.00  148
 47  \w     60.00 100.00   0.50    1.50    --   93.70 -82.00-150.00   80
 48  \w      9.00  86.00   0.50    1.50    --   93.70 -33.00  60.00  154
 49  \w     82.00 108.00   0.50    1.50    --   93.70 -82.00 -30.00   52
 50  \w     73.00  98.00   0.50    1.50    --   93.70 -82.00  30.00   50
 51  \w     11.00  37.00   0.50    1.50    --   93.70 -82.00-150.00   52
 52  \w      5.00 113.00   0.50    1.50    --   93.70 -59.00 150.00  216
 53  \w     10.00 128.00   0.50    1.50    --   93.70  25.00  30.00  236
 54  \w     73.00 105.00   0.50    1.50    --   93.70 -82.00 165.60   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0148726000
_diffrn_orient_matrix_UB_12      0.0827751000
_diffrn_orient_matrix_UB_13      -0.0481922000
_diffrn_orient_matrix_UB_21      -0.0650606000
_diffrn_orient_matrix_UB_22      -0.0537148000
_diffrn_orient_matrix_UB_23      -0.0468520000
_diffrn_orient_matrix_UB_31      -0.0699894000
_diffrn_orient_matrix_UB_32      0.0322964000
_diffrn_orient_matrix_UB_33      0.0454205000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            47701
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.500
_diffrn_reflns_theta_min         3.485
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
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    1.129
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.786
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     513
_refine_ls_number_reflns         8230
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.221
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0946
_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^)+(0.1662P)^2^+1.5640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2749
_refine_ls_wR_factor_ref         0.2958
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6313
_reflns_number_total             8230
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05894d2.cif
_cod_data_source_block           2j-danjing1_auto
_cod_depositor_comments
;
Adding full bibliography for 1568308--1568310.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C48 H60 O8'
_cod_original_formula_weight         764.96
_cod_original_formula_moiety         '2(C24 H30 O4)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        4501.34(17)
_cod_database_code               1568308
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.948
_diffrn_oxdiff_digest_frames
;
01d50762f83e0d74199b9cde2f4bb13fc300029b762
;
_diffrn_oxdiff_digest_hkl
;
01802e3c27259397ef9a5c07a918ecbc675c39
;
_reflns_odcompleteness_completeness 99.92
_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, All O(H) groups
2. Restrained distances
 O4-C24
 1.35 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
O4 \\sim C24 \\sim C21: within 2.7A with sigma of 0.004 and sigma for terminal
atoms of 0.008
C22 \\sim C21 \\sim C20: within 2.7A with sigma of 0.004 and sigma for terminal
atoms of 0.008
4.a Riding coordinates:
 O7(H7), O3(H3)
4.b Ternary CH refined with riding coordinates:
 C33(H33), C12(H12)
4.c Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C40(H40A,H40B), C35(H35A,H35B), C36(H36A,H36B), C15(H15A,
 H15B), C16(H16A,H16B), C11(H11A,H11B), C10(H10A,H10B)
4.d Aromatic/amide H refined with riding coordinates:
 C29(H29), C28(H28), C32(H32), C31(H31), C47(H47), C46(H46), C44(H44),
 C43(H43), C7(H7A), C8(H8), C4(H4), C5(H5), C23(H23), C22(H22), C20(H20),
 C19(H19)
4.e Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C37(H37A,H37B,H37C), C25(H25A,H25B,H25C), C48(H48A,H48B,
 H48C), C17(H17A,H17B,H17C), C9(H9A,H9B,H9C), C1(H1A,H1B,H1C), C24(H24A,H24B,
 H24C)
;
_shelx_res_checksum              94092
_shelx_hkl_checksum              5867
_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 4.126
_oxdiff_exptl_absorpt_empirical_full_min 0.350