Copper-catalyzed synthesis of <i>gem</i>-diborylalkanes by B-H bond insertion of α-furyl boryl carbenes.
Song, Daan; Zhao, Xue; Lu, Fei; Sun, Xinhao; Wang, Guanghui; Xu, Liang; Zhao, Ximei; Organic & biomolecular chemistry 24 (2026) 1440–1446; doi:10.1039/d5ob01996f

data_7160991
_publ_section_title
;
 Copper-catalyzed synthesis of <i>gem</i>-diborylalkanes by B-H bond
 insertion of &#x3b1;-furyl boryl carbenes.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1440
_journal_page_last               1446
_journal_paper_doi               10.1039/d5ob01996f
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C8 H8 B N O5'
_chemical_formula_sum            'C8 H8 B N O5'
_chemical_formula_weight         208.96
_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             2024-12-30
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-09-02 deposited with the CCDC.	2026-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                106.2940(10)
_cell_angle_beta                 90.1950(10)
_cell_angle_gamma                97.3360(10)
_cell_formula_units_Z            4
_cell_length_a                   6.82670(10)
_cell_length_b                   11.0677(2)
_cell_length_c                   13.3937(2)
_cell_measurement_reflns_used    9612
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      4.20
_cell_volume                     962.56(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14117
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.434
_diffrn_reflns_theta_min         4.199
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.022
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1276 before and 0.0602 after correction.
The Ratio of minimum to maximum transmission is 0.5341.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0548
_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^)+(0.0707P)^2^+0.4817P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3187
_reflns_number_total             3419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01996f2.cif
_cod_data_source_block           a
_cod_database_code               7160991
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.905
_shelx_estimated_absorpt_t_min   0.822
_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:
 C7(H7A,H7B), C4(H4A,H4B), C13(H13A,H13B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C1(H1)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C6(H6A,H6B,H6C)
;
_olex2_submission_special_instructions 'No special instructions were received'