From Olefination to Alkylation: In-Situ Halogenation of Julia-Kocienski Intermediates Leading to Formal Nucleophilic Iodo- and Bromodifluoromethylation of Carbonyl Compounds
Yanchuan Zhao; Bing Gao; Jinbo Hu; Journal of the American Chemical Society 134 (2012) 5790–5793; doi:10.1021/ja301601b

data_4117763
_publ_section_title
;
 From Olefination to Alkylation: In-Situ Halogenation of Julia-Kocienski
 Intermediates Leading to Formal Nucleophilic Iodo- and
 Bromodifluoromethylation of Carbonyl Compounds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5790
_journal_page_last               5793
_journal_paper_doi               10.1021/ja301601b
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H12 Br2 F N O'
_chemical_formula_weight         425.10
_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                   5.876(3)
_cell_length_b                   15.458(9)
_cell_length_c                   17.174(10)
_cell_measurement_reflns_used    2363
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      25.84
_cell_measurement_theta_min      2.64
_cell_volume                     1559.9(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0681
_diffrn_reflns_av_sigmaI/netI    0.0756
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11087
_diffrn_reflns_theta_full        26.53
_diffrn_reflns_theta_max         26.53
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    5.207
_exptl_absorpt_correction_T_max  0.9030
_exptl_absorpt_correction_T_min  0.3041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.474
_refine_diff_density_min         -1.170
_refine_diff_density_rms         0.151
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0660P)^2^+3.0075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1394
_reflns_number_gt                2561
_reflns_number_total             3209
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja301601b_si_003.cif
_cod_data_source_block           mo_dm11507_0m
_cod_original_cell_volume        1559.8(15)
_cod_database_code               4117763