Copper-Catalyzed Borylative Aromatization of p-Quinone Methides: Enantioselective Synthesis of Dibenzylic Boronates.
Jarava-Barrera, Carlos; Parra, Alejandro; López, Aurora; Cruz-Acosta, Fabio; Collado-Sanz, Daniel; Cárdenas, Diego J; Tortosa, Mariola; ACS catalysis 6 (2016) 442–446; doi:10.1021/acscatal.5b02742

data_4513784
_publ_section_title
;
 Copper-Catalyzed Borylative Aromatization of p-Quinone Methides:
 Enantioselective Synthesis of Dibenzylic Boronates.
;
_journal_issue                   1
_journal_name_full               'ACS catalysis'
_journal_page_first              442
_journal_page_last               446
_journal_paper_doi               10.1021/acscatal.5b02742
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H38 B Br O3'
_chemical_formula_weight         501.29
_chemical_name_common            CJ802
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   13.3911(3)
_cell_length_b                   13.3911(3)
_cell_length_c                   26.1903(7)
_cell_measurement_reflns_used    6881
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      20.3127
_cell_measurement_theta_min      2.3353
_cell_volume                     4067.28(17)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            35365
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    1.540
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.303
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0689P)^2^+0.3054P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1257
_reflns_number_gt                3510
_reflns_number_total             4945
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs5b02742_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments
;Adding full bibliography for 4513784.cif.

 Adding full bibliography for 4513784.cif.
;
_cod_database_code               4513784