Expanded Substrate Scope and Improved Reactivity of Ether-Forming Cross-Coupling Reactions of Organotrifluoroborates and Acetals
Cam-Van T. Vo; T. Andrew Mitchell; Jeffrey W. Bode; Journal of the American Chemical Society 133 (2011) 14082–14089; doi:10.1021/ja205174c

data_4106702
_publ_contact_author_address
;

;
_publ_contact_author_email       schweizer@org.chem.ethz.ch
_publ_contact_author_name        'B. Schweizer'
_publ_section_title
;
 Expanded Substrate Scope and Improved Reactivity of Ether-Forming
 Cross-Coupling Reactions of Organotrifluoroborates and Acetals
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14082
_journal_page_last               14089
_journal_paper_doi               10.1021/ja205174c
_journal_volume                  133
_journal_year                    2011
_chemical_compound_source        'LOC ETH Zurich'
_chemical_formula_moiety         'C9 H11 B F N O2 '
_chemical_formula_sum            'C9 H11 B F N O2'
_chemical_formula_weight         195.001
_chemical_name_systematic
;
2-fluoro-4,5-dimethyl-2-phenyl-1,3,4,2-dioxazaborol-4-ium-2-uide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.2905(3)
_cell_length_b                   10.0263(3)
_cell_length_c                   23.1917(8)
_cell_measurement_reflns_used    10143
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     1927.76(11)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.04533
_diffrn_orient_matrix_UB_12      -0.00782
_diffrn_orient_matrix_UB_13      0.11150
_diffrn_orient_matrix_UB_21      0.00682
_diffrn_orient_matrix_UB_22      -0.09903
_diffrn_orient_matrix_UB_23      -0.00971
_diffrn_orient_matrix_UB_31      0.03985
_diffrn_orient_matrix_UB_32      0.00430
_diffrn_orient_matrix_UB_33      -0.01590
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            4125
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       Cube
_exptl_crystal_F_000             816
_exptl_crystal_size_max          .33
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .105
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0412
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1441
_reflns_number_gt                1725
_reflns_number_total             2157
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja205174c_si_003.cif
_cod_data_source_block           global
_cod_original_sg_symbol_H-M      'P b c a '
_cod_original_formula_sum        'C9 H11 B F N O2 '
_cod_database_code               4106702