Electrochemical radical borylation of N-heterocycles with NHC-boranes: efficient access to the B–N bond
Chang, Hong; Zhuang, Shiyi; Wang, Jie; Dong, Mengmeng; Liu, Chenjiang; Jin, Weiwei; Green Chemistry 28 (2026) 3541–3548; doi:10.1039/D5GC06005B

data_7251585
_publ_section_title
;
 Electrochemical radical borylation of N-heterocycles with NHC-boranes:
 efficient access to the B--N bond
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              3541
_journal_page_last               3548
_journal_paper_doi               10.1039/D5GC06005B
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C17 H18 B N3'
_chemical_formula_sum            'C17 H18 B N3'
_chemical_formula_weight         275.15
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-05-15 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.777(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.575(5)
_cell_length_b                   8.029(3)
_cell_length_c                   25.514(8)
_cell_measurement_reflns_used    2220
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.00
_cell_measurement_theta_min      2.52
_cell_volume                     3111.6(18)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            16821
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.408
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1271 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.7119.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         6326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1560
_refine_ls_R_factor_gt           0.0715
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0987P)^2^+0.9703P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1826
_refine_ls_wR_factor_ref         0.2315
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3095
_reflns_number_total             6326
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc06005b2.cif
_cod_data_source_block           220603znn1_0m
_cod_depositor_comments
'Adding full bibliography for 7251584--7251586.cif.'
_cod_original_cell_volume        3111.6(17)
_cod_database_code               7251585
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H,H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 B014(H01G,H01H), B016(H01O,H01P)
2.b Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C012(H012)
2.c Idealised Me refined as rotating group:
 C010(H01A,H01B,H01C), C011(H01D,H01E,H01F), C013(H01I,H01J,H01K), C015(H01L,
 H01M,H01N)
;
_shelx_res_checksum              89608
_shelx_hkl_checksum              86258
_olex2_submission_special_instructions 'No special instructions were received'