Highly diastereoselective synthesis of borylcyclopropanes by copper-catalyzed borylcyclopropanation of alkenes with enynones
Lu, Fei; Song, Daan; Sun, Xinhao; Zhi, Ling; Liu, Xiaoyun; Zhao, Ximei; Wang, Guanghui; Chemical Communications  (2026) –; doi:10.1039/D6CC00756B

data_7135738
_publ_section_title
;
 Highly diastereoselective synthesis of borylcyclopropanes by
 copper-catalyzed borylcyclopropanation of alkenes with enynones.
;
_journal_issue                   36
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9213
_journal_page_last               9217
_journal_paper_doi               10.1039/d6cc00756b
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C25 H26 B Fe N O6'
_chemical_formula_sum            'C25 H26 B Fe N O6'
_chemical_formula_weight         503.13
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-07-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2026-02-02 deposited with the CCDC.	2026-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.3287(4)
_cell_length_b                   11.5160(4)
_cell_length_c                   30.4997(9)
_cell_measurement_reflns_used    4275
_cell_measurement_temperature    174.00
_cell_measurement_theta_max      69.425
_cell_measurement_theta_min      2.897
_cell_volume                     4681.5(3)
_computing_cell_refinement       'SAINT V8.41 (?, 2016)'
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      174.00
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            20718
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        66.588
_diffrn_reflns_theta_max         66.588
_diffrn_reflns_theta_min         2.898
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    5.520
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5014
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1136 before and 0.0708 after correction.
The Ratio of minimum to maximum transmission is 0.6656.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       block
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         4039
_refine_ls_number_restraints     343
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0977
_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^)+(0.0001P)^2^+31.8987P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1821
_refine_ls_wR_factor_ref         0.1982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2986
_reflns_number_total             4039
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00756b2.cif
_cod_data_source_block           cu_20250723_wgh_33_2_a
_cod_depositor_comments          'Adding full bibliography for 7135738.cif.'
_cod_database_code               7135738
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.733
_shelx_estimated_absorpt_t_min   0.557
_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. Restrained distances
 C4-C7 \\sim C4A-C7A
 with sigma of 0.04
 C3-C6 \\sim C3A-C6A
 with sigma of 0.04
 C5-C10 \\sim C5A-C10A
 with sigma of 0.04
 C3-C10 \\sim C3A-C10A
 with sigma of 0.04
 C5-C6 \\sim C5A-C6A
 with sigma of 0.04
 C6-C8 \\sim C6A-C8
 with sigma of 0.04
 C3-C4 \\sim C3A-C4A
 with sigma of 0.04
 C3-C8 \\sim C3A-C8
 with sigma of 0.04
 C4-C5 \\sim C4A-C5A
 with sigma of 0.04
 C4-C9 \\sim C4A-C9A
 with sigma of 0.04
 C5-C8 \\sim C5A-C8
 with sigma of 0.04
 C6-C10 \\sim C6A-C10A
 with sigma of 0.02
 C7-C9 \\sim C7A-C9A
 with sigma of 0.04
 C8-C9 \\sim C8-C9A
 with sigma of 0.04
 C9-C10 \\sim C9A-C10A
 with sigma of 0.02
 Fe1-C1 \\sim Fe1A-C1A
 with sigma of 0.04
 Fe1-C2 \\sim Fe1A-C2A
 with sigma of 0.04
 Fe1-C3 \\sim Fe1A-C3A
 with sigma of 0.04
 C3-C5 \\sim C3A-C5A
 with sigma of 0.04
 Fe1-C4 \\sim Fe1A-C4A
 with sigma of 0.04
 C3-C7 \\sim C3A-C7A
 with sigma of 0.04
 Fe1-C5 \\sim Fe1A-C5A
 with sigma of 0.04
 C3-C9 \\sim C3A-C9A
 with sigma of 0.04
 Fe1-C6 \\sim Fe1A-C6A
 with sigma of 0.04
 Fe1-C7 \\sim Fe1A-C7A
 with sigma of 0.04
 Fe1-C8 \\sim Fe1A-C8
 with sigma of 0.04
 Fe1-C9 \\sim Fe1A-C9A
 with sigma of 0.04
 Fe1-C10 \\sim Fe1A-C10A
 with sigma of 0.04
 C4-C6 \\sim C4A-C6A
 with sigma of 0.04
 C4-C8 \\sim C4A-C8
 with sigma of 0.04
 C4-C10 \\sim C4A-C10A
 with sigma of 0.04
 C5-C7 \\sim C5A-C7A
 with sigma of 0.04
 C5-C9 \\sim C5A-C9A
 with sigma of 0.04
 C1-C2 \\sim C1A-C2A
 with sigma of 0.04
 C1-C3 \\sim C1A-C3A
 with sigma of 0.04
 C1-C4 \\sim C1A-C4A
 with sigma of 0.04
 C1-C5 \\sim C1A-C5A
 with sigma of 0.04
 C1-C6 \\sim C1A-C6A
 with sigma of 0.04
 C1-C7 \\sim C1A-C7A
 with sigma of 0.04
 C1-C8 \\sim C1A-C8
 with sigma of 0.04
 C6-C7 \\sim C6A-C7A
 with sigma of 0.04
 C1-C9 \\sim C1A-C9A
 with sigma of 0.04
 C6-C9 \\sim C6A-C9A
 with sigma of 0.04
 C1-C10 \\sim C1A-C10A
 with sigma of 0.04
 C7-C8 \\sim C7A-C8
 with sigma of 0.04
 C7-C10 \\sim C7A-C10A
 with sigma of 0.04
 C2-C3 \\sim C2A-C3A
 with sigma of 0.04
 C2-C4 \\sim C2A-C4A
 with sigma of 0.04
 C8-C10 \\sim C8-C10A
 with sigma of 0.04
 C2-C5 \\sim C2A-C5A
 with sigma of 0.04
 C2-C6 \\sim C2A-C6A
 with sigma of 0.04
 C2-C7 \\sim C2A-C7A
 with sigma of 0.04
 C2-C8 \\sim C2A-C8
 with sigma of 0.04
 C2-C9 \\sim C2A-C9A
 with sigma of 0.04
 C2-C10 \\sim C2A-C10A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Fe1 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8
\\sim C9 \\sim C10 \\sim Fe1A \\sim C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A
\\sim C6A \\sim C7A \\sim C9A \\sim C10A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(Fe1A)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=
 Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C9A)=
 Sof(H9A)=Sof(C10A)=Sof(H10A)=1-FVAR(1)
 Sof(Fe1)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=
 Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(C9)=Sof(H9)=Sof(C10)=
 Sof(H10)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C11(H11)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C22(H22A,H22B), C24(H24A,H24B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10),
 C15(H15), C1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A),
  C9A(H9A), C10A(H10A)
5.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              91553
_shelx_hkl_checksum              7018
_olex2_submission_special_instructions 'No special instructions were received'