β-Boron or β-Silicon Effect Enables a Regioselective Ni-Catalyzed Hydrocyanation of Internal Alkynes
Wang, Honggen; Chen, Zhi-Hao; Lin, Shuang; Kang, Xinman; Huang, Jiawu; Qian, Jiasheng; Li, Qingjiang; Green Chemistry  (2026) –; doi:10.1039/D6GC00727A

data_7251813
_publ_section_title
;
 \b-Boron or \b-silicon effect enables a regioselective Ni-catalyzed
 hydrocyanation of internal alkynes
;
_journal_issue                   16
_journal_name_full               'Green Chemistry'
_journal_page_first              7040
_journal_page_last               7048
_journal_paper_doi               10.1039/D6GC00727A
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C13 H19 B N2 O4'
_chemical_formula_sum            'C13 H19 B N2 O4'
_chemical_formula_weight         278.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-08-02 deposited with the CCDC.	2026-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.812(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1742(2)
_cell_length_b                   20.2220(4)
_cell_length_c                   10.1873(2)
_cell_measurement_reflns_used    6145
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.4020
_cell_measurement_theta_min      2.1630
_cell_volume                     1451.70(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.956
_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   -103.00 -75.00   0.50    0.17    -- -100.00  77.00 -90.00   56
  2  \w    -63.00 -36.00   0.50    0.17    -- -100.00  77.00 -90.00   54
  3  \w    -52.00 -26.00   0.50    0.17    -- -100.00  61.00  30.00   52
  4  \w    -62.00 -27.00   0.50    0.17    -- -100.00  61.00  90.00   70
  5  \w    -60.00 -34.00   0.50    0.17    -- -100.00  61.00  60.00   52
  6  \w    -69.00 -34.00   0.50    0.17    -- -100.00  61.00   0.00   70
  7  \w    -53.00 -27.00   0.50    0.17    -- -100.00  49.00-105.00   52
  8  \w   -112.00 -54.00   0.50    0.17    -- -100.00 125.00  60.00  116
  9  \w   -173.00 -81.00   0.50    0.17    -- -100.00 -49.00 107.00  184
 10  \w   -117.00 -28.00   0.50    0.05    --  -44.84 -49.00 107.00  178
 11  \w     72.00  97.00   0.50    0.05    --   44.84  49.00-105.00   50
 12  \w    111.00 174.00   0.50    0.17    --  105.85  61.00-180.00  126
 13  \w    137.00 169.00   0.50    0.17    --  105.85  49.00-105.00   64
 14  \w    112.00 177.00   0.50    0.17    --  105.85  61.00 150.00  130
 15  \w     34.00 103.00   0.50    0.17    --  105.85 -77.00  60.00  138
 16  \w     34.00  68.00   0.50    0.17    --  105.85 -61.00 120.00   68
 17  \w     44.00  71.00   0.50    0.17    --  105.85 -61.00 150.00   54
 18  \w    -10.00  15.00   0.50    0.05    --   44.84 -49.00 107.00   50
 19  \w     40.00  73.00   0.50    0.17    --  105.85 -61.00 -30.00   66
 20  \w    -31.00  27.00   0.50    0.05    --   44.84 -19.00 -60.00  116
 21  \w     57.00  83.00   0.50    0.05    --   44.84-125.00 -60.00   52
 22  \w     39.00  89.00   0.50    0.17    --  105.85 -94.00 -30.00  100
 23  \w    -29.00  28.00   0.50    0.05    --  -44.84  49.00-105.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0356587000
_diffrn_orient_matrix_UB_12      0.0459035000
_diffrn_orient_matrix_UB_13      0.1134508000
_diffrn_orient_matrix_UB_21      0.2143946000
_diffrn_orient_matrix_UB_22      0.0009611000
_diffrn_orient_matrix_UB_23      0.0577677000
_diffrn_orient_matrix_UB_31      0.0236371000
_diffrn_orient_matrix_UB_32      0.0607600000
_diffrn_orient_matrix_UB_33      -0.0866236000
_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  0.0435
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9189
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.547
_diffrn_reflns_theta_min         4.373
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0685P)^2^+0.3537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1254
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2499
_reflns_number_total             2863
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6gc00727a2.cif
_cod_data_source_block           chenzhh_230522_auto
_cod_depositor_comments          'Adding full bibliography for 7251813.cif.'
_cod_database_code               7251813
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     CHONB
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.862
_reflns_odcompleteness_completeness 99.93
_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:
 C008(H00A,H00B), C009(H00C,H00D), C00D(H00H,H00I), C00F(H00J,H00K), C00H(H00M,
 H00N), C00I(H00O,H00P)
2.b Aromatic/amide H refined with riding coordinates:
 C00G(H00L)
2.c Idealised Me refined as rotating group:
 C00B(H00E,H00F,H00G), C00K(H00Q,H00R,H00S)
;
_shelx_res_checksum              8390
_shelx_hkl_checksum              42831
_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 1.553
_oxdiff_exptl_absorpt_empirical_full_min 0.475