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_4516722
_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         'C29 H22 Cl Cu N3 O2'
_chemical_formula_sum            'C29 H22 Cl Cu N3 O2'
_chemical_formula_weight         543.48
_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_secondary   iterative
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.3940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5811(4)
_cell_length_b                   8.8795(3)
_cell_length_c                   17.1799(5)
_cell_measurement_reflns_used    7675
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.62
_cell_measurement_theta_min      2.39
_cell_volume                     2362.09(12)
_computing_cell_refinement       'Saint+ ver. V8.34A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (Bruker AXS)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2012)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23751
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.674
_diffrn_source                   'rotating anode (Nonius FR-591)'
_exptl_absorpt_coefficient_mu    1.072
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SadAbs 2014/5 (Bruker AXS)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       needle
_exptl_crystal_F_000             1116
_exptl_crystal_size_max          0.386
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_min          0.134
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0335P)^2^+2.0820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0778
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3915
_reflns_number_total             4633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b02918_si_002.cif
_cod_data_source_block           MaHa140_multiscan_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4516722
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.682
_shelx_estimated_absorpt_t_max   0.870