Enantioselective Synthesis of Axially Chiral Biaryls by the Pd-Catalyzed Suzuki-Miyaura Reaction: Substrate Scope and Quantum Mechanical Investigations
Xiaoqiang Shen; Gavin O. Jones; Donald A. Watson; Brijesh Bhayana; Stephen L. Buchwald; Journal of the American Chemical Society 132 (2010) 11278–11287; doi:10.1021/ja104297g

data_4102831
_publ_section_title
;
 Enantioselective Synthesis of Axially Chiral Biaryls by the Pd-Catalyzed
 Suzuki-Miyaura Reaction: Substrate Scope and Quantum Mechanical
 Investigations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11278
_journal_page_last               11287
_journal_paper_doi               10.1021/ja104297g
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C51 H62 Cl3 N O P2 Pd'
_chemical_formula_weight         979.71
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 109.2100(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.4996(7)
_cell_length_b                   20.2853(15)
_cell_length_c                   12.8980(10)
_cell_measurement_temperature    100(2)
_cell_volume                     2347.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            54326
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  0.9482
_exptl_absorpt_correction_T_min  0.8772
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1020
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.703
_refine_diff_density_min         -1.261
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.027(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.509
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         13660
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.509
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0572
_refine_ls_wR_factor_ref         0.0587
_reflns_number_gt                12516
_reflns_number_total             13660
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja104297g_si_002.cif
_cod_data_source_block           07201_0m
_cod_database_code               4102831