Highly Efficient Synthesis of Alkylboronate Esters via Cu(II)-Catalyzed Borylation of Unactivated Alkyl Bromides and Chlorides in Air
Bose, Shubhankar Kumar; Brand, Simon; Omoregie, Helen Oluwatola; Haehnel, Martin; Maier, Jonathan; Bringmann, Gerhard; Marder, Todd B.; ACS Catalysis 6 (2016) 8332–; doi:10.1021/acscatal.6b02918

data_4516720
_publ_section_title
;
 Highly Efficient Synthesis of Alkylboronate Esters via Cu(II)-Catalyzed
 Borylation of Unactivated Alkyl Bromides and Chlorides in Air
;
_journal_issue                   12
_journal_name_full               'ACS Catalysis'
_journal_page_first              8332
_journal_paper_doi               10.1021/acscatal.6b02918
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C26 H23 Cl Cu N2 O3'
_chemical_formula_sum            'C26 H23 Cl Cu N2 O3'
_chemical_formula_weight         510.45
_space_group_crystal_system      orthorhombic
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_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
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_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.278(2)
_cell_length_b                   17.113(3)
_cell_length_c                   20.133(3)
_cell_measurement_reflns_used    9783
_cell_measurement_temperature    168(2)
_cell_measurement_theta_max      28.74
_cell_measurement_theta_min      2.38
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_computing_cell_refinement       'Saint+ ver. V8.34A (Bruker AXS)'
_computing_data_collection       'Smart NT ver. 5.63 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (Bruker AXS)'
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_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2012)'
_diffrn_ambient_temperature      168(2)
_diffrn_detector                 'CCD area detector (Apex1)'
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_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART-APEX'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
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_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            77083
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.784
_diffrn_reflns_theta_min         2.023
_diffrn_source                   'sealed tube'
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_exptl_absorpt_correction_T_max  0.6751
_exptl_absorpt_correction_T_min  0.5707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SadAbs 2014/5 (Bruker AXS)'
_exptl_crystal_colour            green
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_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.480
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+2.2347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                5356
_reflns_number_total             5945
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b02918_si_002.cif
_cod_data_source_block           MaHa111_multiscan
_cod_original_cell_volume        4574.6(13)
_cod_database_code               4516720
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.557
_shelx_estimated_absorpt_t_max   0.620