Copper-Catalyzed B-H Bond Insertion Reaction: A Highly Efficient and Enantioselective C-B Bond-Forming Reaction with Amine-Borane and Phosphine-Borane Adducts
Qing-Qing Cheng; Shou-Fei Zhu; Yong-Zhen Zhang; Xiu-Lan Xie; Qi-Lin Zhou; Journal of the American Chemical Society 135 (2013) 14094–14097; doi:10.1021/ja408306a

data_4120864
_publ_section_title
;
 Copper-Catalyzed B-H Bond Insertion Reaction: A Highly Efficient and
 Enantioselective C-B Bond-Forming Reaction with Amine-Borane and
 Phosphine-Borane Adducts
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14094
_journal_page_last               14097
_journal_paper_doi               10.1021/ja408306a
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C16 H18 B Cl2 O2 P'
_chemical_formula_weight         354.98
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.142(2)
_cell_length_b                   11.748(2)
_cell_length_c                   15.056(3)
_cell_measurement_reflns_used    5334
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      2.199
_cell_volume                     1793.9(6)
_computing_cell_refinement       crystalclear
_computing_data_collection       'crystalclear(Rigaku/MSC Inc., 2005)'
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'rigaku saturn CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14293
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_T_max  0.9229
_exptl_absorpt_correction_T_min  0.8990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_extinction_coef       0.0493(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0753
_reflns_number_gt                2494
_reflns_number_total             3159
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja408306a_si_002.cif
_cod_data_source_block           r100813a1
_cod_database_code               4120864